Fused bicyclic heterocycle derivatives as pesticides

ABSTRACT

The invention relates to novel compounds of the formula (I) 
     
       
         
         
             
             
         
       
     
     in which Aa, Ab, Ac, Ad, R 1 , Q and n have the definitions given above,
 
to their use as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for their preparation.

The present invention relates to novel fused bicyclic heterocyclederivatives of the formula (I), to their use as acaricides and/orinsecticides for controlling animal pests, particularly arthropods andespecially insects and arachnids, and to processes and intermediates fortheir preparation.

Fused bicyclic heterocycle derivatives having insecticidal propertieshave already been described in the literature, for example in WO2010/125985, WO 2012/074135, WO 2012/086848, WO 2013/018928, WO2013/191113, WO 2014/142292, WO 2014/148451, WO 2015/000715, WO2016/124563, WO 2016/124557, PCT/EP/2016/057389, PCT/EP2016/078989,PCT/EP2017/050773, PCT/EP2017/057397, EP 16168252.1, EP17154789.6, WO2015/121136, WO 2015/002211, WO 2015/071180, WO 2016/020286, WO2015/059039, WO2015/190316, WO 2016/091731, WO 2016/107742. WO2016/162318, PCT/EP2016/075365, WO 2017/055185. EP 16180170.9, EP16189445.6, EP 16200177.0, EP17153317.7, WO 2016/129684, WO 2017/061497.

However, some of the active ingredients already known from the documentscited above have disadvantages in use, whether in that they have only anarrow spectrum of application or in that they do not have satisfactoryinsecticidal or acaricidal activity.

Novel fused bicyclic heterocycle derivatives have now been found, thesehaving advantages over the compounds already known, examples of whichinclude better biological or environmental properties, a wider range ofapplication methods, better insecticidal or acaricidal action, and goodcompatibility with crop plants. The fused bicyclic heterocyclederivatives can be used in combination with further agents for improvingefficacy, especially against insects that are difficult to control.

The present invention therefore provides novel compounds of the formula(I)

in which (configuration 1)Aa is —N(R⁷)—, —S(O)_(m)—, —O—, —C(R⁸)(R⁹) or carbonyl,Ab is —N(R⁷)—, —S(O)_(m)—, —O—, —C(R¹⁰)(R¹¹)— or carbonyl,Ac is —N(R⁷)—, —S(O)_(m)—, —O—, —C(R¹²)(R¹³)— or carbonyl,Ad is —N(R⁷), —S(O)_(m)—, —O—, —C(R¹⁴)(R¹⁵)— or carbonyl,where not more than two of the Aa, Ab, Ac and Ad substituents at thesame time can be —N(R⁷)—, —O— or

—S(O)_(m)—.

-   R¹ is (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl, amino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkyl-amino, (C₃-C₈)-cycloalkylamino,    (C₁-C₆)-alkylcarbonylamino, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfonylamino, aminosulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl, di(C₁-C₆)    alkylaminosulfonyl-(C₁-C₆)-alkyl.    -   or is in each case optionally identically or differently mono-        or poly-aryl-, -hetaryl- or -heterocyclyl-substituted        (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,        (C₃-C₈)-cycloalkyl, where aryl, hetaryl or heterocyclyl may each        optionally be mono- or polysubstituted identically or        differently by halogen, cyano, nitro, hydroxyl, amino, carboxyl,        carbamoyl, aminosulfonyl, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,        (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy,        (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl,        (C₁-C₆)-alkylsulfimino, (C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl,        (C₁-C₆)-alkylsulfoximino,        (C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl,        (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkylcarbonyl,        (C₃-C₆)-trialkylsilyl or benzyl, or-   R¹ is aryl, hetaryl or heterocyclyl, each of which is optionally    mono- or polysubstituted identically or differently by halogen,    cyano, nitro, hydroxyl, amino, carboxyl, carbamoyl, (C₁-C₆)-alkyl,    (C₃-C₈)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆-haloalkyl,    (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylsulfimino,    (C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkylsulfoximino, (C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkylcarbonyl,    (C₃-C₆)-trialkylsilyl, (═O) (in the case of heterocyclyl only) or    (═O)₂ (in the case of heterocyclyl only),-   R⁸, R⁹. R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are independently hydrogen,    cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri-(C₁-C₆)-alkylsilyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl.    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,    (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,    (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,    (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,    (C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,    (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino),    -   are in each case optionally singly or multiply, identically or        differently substituted aryl or hetaryl, where (in the case of        hetaryl) at least one carbonyl group may optionally be present        and/or where possible substituents in each case are as follows:        cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,        tri-(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,        (C₃-C₈)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl,        (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,        (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl (C₂-C₆)cyanoalkynyl,        (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,        (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy,        (C₁-C₆)alkoxy-(C₁-C₆)alkoxy, (C₁-C₆)alkylhydroxyimino,        (C₁-C₆)alkoxyimino, (C₁-C₆)alkyl-(C₁-C₆)alkoxyimino,        (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)alkylthio.        (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,        (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,        (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,        (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,        (C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,        (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,        (C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl,        (C₁-C₆)alkylcarbonyloxy, (C₁-C₆)alkoxycarbonyl,        (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,        (C₂-C₆)alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,        (C₃-C₆)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,        (C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, aminosulfonyl,        (C₁-C₆)alkylaminosulfonyl, di-(C₁-C₆)alkylaminosulfonyl,        (C₁-C₆)alkylsulfoximino, aminothiocarbonyl,        (C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,        (C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino.-   R⁷ is hydrogen, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl,    (C₁-C₆)hydroxyalkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,    (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl,    (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,    (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkynyl,    (C₃-C₈)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₈)cycloalkyl,    (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl, halo(C₃-C₈)cycloalkyl,    (C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl,    (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl or    (C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl.-   Q is a partly saturated or saturated heterocyclic or heteroaromatic    8-, 9-, 10-, 11- or 12-membered fused bicyclic or tricyclic ring    system where at least one carbonyl group may optionally be present    and/or where the ring system is optionally mono- or polysubstituted    identically or differently, and where the substituents may    independently be selected from cyano, halogen, nitro, acetyl,    hydroxyl, amino, SCN, tri-(C₁-C₆)-alkylsilyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy-(C₁-C₄)-alkyl,    (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy,    (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,    (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,    (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio.    (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,    (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkyl-aminocarbonyl, di-(C₁-C₆)-alkyl-aminothiocarbonyl,    (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,    (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkyl-aminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino),    -   or where the substituents may independently be selected from        phenyl or a 5- or 6-membered heteroaromatic ring, where phenyl        or the ring may optionally be mono- or polysubstituted        identically or differently by C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,        C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl,        halogen, CN, NO₂, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,-   m is 0, 1 or 2,-   n is 0, 1 or 2.

It has additionally been found that the compounds of the formula (I)have very good efficacy as pesticides, preferably as insecticides and/oracaricides, and additionally generally have very good plantcompatibility, in particular with respect to crop plants.

The compounds according to the invention are defined in general terms bythe formula (I). Preferred substituents or ranges of the radicals givenin the formulae mentioned above and below are illustrated hereinafter:

Configuration 2-1

-   Aa is preferably —S(O)_(m)—, —O—, —C(R⁸)(R⁹)— or carbonyl,-   Ab is preferably —N(R⁷)—, —S(O)_(m)—, —O—, or —C(R¹⁰)(R¹¹)—,-   Ac is preferably —N(R⁷)—, —C(R¹²)(R¹³)— or carbonyl,-   Ad is preferably —N(R⁷)—, —O—, or —C(R¹⁴)(R¹⁵)—,    where not more than two of the Aa, Ab, Ac and Ad substituents at the    same time can be —N(R⁷)—, —O— or-   —S(O)_(m)—,    preferably resulting in the following structural units A1 to A11:

where the bond to the substituent Q is identified by a wavy line and thebond to the sulfur atom by an asterisk *,

-   -   R¹ is preferably (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl,        (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,        (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,        (C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,        (C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkylamino, di-(C₁-C₄)alkyl-amino,        (C₃-C₆)cycloalkylamino, (C₁-C₄)alkylcarbonylamino,        (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl,        (C₁-C₄)haloalkylsulfinyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,        (C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfonylamino, or is in each case optionally        identically or differently mono- or di-aryl-, -hetaryl- or        -heterocyclyl-substituted (C₁-C₄)alkyl, (C₁-C₄)alkoxy,        (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl, where aryl        hetaryl or heterocyclyl may each optionally identically or        differently be mono- or disubstituted by halogen, cyano,        carbamoyl, aminosulfonyl, (C₁-C₄)alkyl, (C₃-C₄)cycloalkyl,        (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,        (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)alkylsulfimino, or

-   R¹ is preferably aryl, hetaryl or heterocyclyl, each of which is    optionally mono- or disubstituted identically or differently by    halogen, cyano, carbamoyl, (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-alkylsulfimino, (C₁-C₄)-alkylsulfoximino,    (C₁-C₄)-alkylcarbonyl, (C₃-C₄)-trialkylsilyl, (═O) (in the case of    heterocyclyl only) or (═O)₂ (in the case of heterocyclyl only),

-   R⁸, R⁹, R¹⁰. R¹¹, R¹², R¹³. R¹⁴. R¹⁵ are preferably independently    hydrogen, cyano, halogen, nitro, acetyl, hydroxyl, amino. SCN,    tri-(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,    (C₃-C₈)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy,    (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₄)alkylhydroxyimino,    (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxy imino,    (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,    (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,    di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino.    (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulfonyl,    (C₁-C₄)alkylaminosulfonyl, di-(C₁-C₄)alkylaminosulfonyl,    aminothiocarbonyl, NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino),    -   and also preferably are phenyl or hetaryl, each of which is        optionally mono- or disubstituted identically or differently,        where (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, halogen, nitro, acetyl, amino,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,        (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,        (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy,        (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₄)alkylhydroxyimino,        (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,        (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,        (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,        (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,        (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,        di-(C₁-C₄)alkylaminosulfonyl. NHCO—(C₁-C₄)alkyl        ((C₁-C₄)alkylcarbonylamino),

-   R⁷ is preferably hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,    (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,

-   Q is preferably a heteroaromatic 8-, 9-, 10-, 11- or 12-membered    fused bicyclic or tricyclic ring system, where the ring system is    optionally mono- or polysubstituted identically or differently and    where the substituents may independently be selected from cyano,    halogen, nitro, acetyl, hydroxyl, amino, SCN,    tri-(C₁-C₆)-alkylsilyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₆)-haloalkynyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁—C)-alkylhydroxyimino,    (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,    (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio. (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,    (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,    (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino),    -   or where the substituents may independently be selected from        phenyl or a 5- or 6-membered heteroaromatic ring, where phenyl        or the ring may optionally be mono- or polysubstituted        identically or differently by C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,        C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl,        halogen, CN, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,

-   n is preferably 0, 1 or 2,

-   m is preferably 0, 1 or 2.

Configuration 2-2

-   Q, R¹, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the    definitions given in configuration 2-1 and-   Aa is preferably —S(O)_(m)—, —O—, —C(R⁸)(R⁹)— or carbonyl,-   Ab is preferably —N(R⁷)—, —S(O)_(m)—, —O— or —C(R¹⁰)(R¹¹)—,-   Ac is preferably —N(R⁷)—, —C(R¹²)(R¹³)— or carbonyl,-   Ad is preferably —N(R⁷)—, —O— or —C(R¹⁴)(R¹¹)—,    where not more than two of the Aa, Ab, Ac and Ad substituents at the    same time can be —N(R⁷)—, —O— or-   —S(O)_(m)—,    preferably resulting in the following structural units A1 to A12:

where the bond to the substituent Q is identified by a wavy line and thebond to the sulfur atom by an asterisk *.

Configuration 3-1

-   Aa is more preferably —S(O)_(m)—, —O—, or —C(R⁸)(R⁹)—,-   Ab is more preferably —S(O)_(m)—, —O—, or —C(R¹⁰)(R¹¹)—,-   Ac is more preferably —C(R¹²)(R¹³)—,-   Ad is more preferably —O—, or —C(R¹⁴)(R¹¹)—,-   where not more than two of the Aa, Ab and Ad substituents at the    same time can be —O— or —S(O)_(m)—, more preferably resulting in the    following structural units: A1. A4, A6, A7, A8. A9,-   R¹ is more preferably (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,-   R⁸, R⁹, R¹⁰, R¹¹, R¹². R¹³, R¹⁴, R¹⁵ are more preferably    independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, SCN,    tri-(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,    (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkylhydroxyimino,    (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)alkylthio. (C₁-C₄)haloalkylthio. (C₁-C₄)alkylsulfinyl,    (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,    (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,    aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,    di-(C₁-C₄)alkylaminosulfonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino), and also more preferably are phenyl or    hetaryl, each of which is optionally mono- or disubstituted    identically or differently, where (in the case of hetaryl) at least    one carbonyl group may optionally be present and/or where possible    substituents are in each case as follows: cyano, halogen.    (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₂-C₄)alkenyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,    (C₁-C₄)haloalkoxy, (C₁-C₄)alkylhydroxyimino. (C₁-C₄)alkoxyimino,    (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,    (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,    (C₁-C₆)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,    (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,    aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,    di-(C₁-C₄)alkylaminosulfonyl. NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino),-   R⁷ is more preferably hydrogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,    (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    haloC₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,    (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl    or (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,-   Q is more preferably a heteroaromatic 9-membered or 12-membered    fused bicyclic or tricyclic ring system from the group of Q1 to Q20,

-   R⁴ is more preferably (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)Cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl or    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,-   R⁵, R⁶ are independently more preferably hydrogen, cyano, halogen.    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio.    (C₁-C₄)-haloalkylthio. (C₁-C₄)-alkylsulfinyl,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyloxy,    (C₁-C₄)-alkylcarbonyl, (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,    (C₁-C₄)-alkylsulfonylamino, (C₁-C₄)-alkylamino,    di-(C₁-C₄)-alkylamino, aminosulfonyl, (C₁-C₄)-alkylaminosulfonyl or    di-(C₁-C₄)-alkylaminosulfonyl,-   n is more preferably 0, 1 or 2,-   m is more preferably 0, 1 or 2.

Configuration 3-2

-   Aa is more preferably —S(O)_(m)—, —O—, —C(R⁸)(R⁹)— or carbonyl,-   Ab is more preferably —S(O)_(m)—, —O— or —C(R¹⁰)(R¹¹)—,-   Ac is more preferably —C(R¹²)(R¹³)—,-   Ad is more preferably —O— or —C(R¹⁴)(R¹⁵)—,    where not more than two of the Aa, Ab and Ad substituents at the    same time can be —O— or —S(O)_(m)—, more preferably resulting in the    following structural units: A1, A4, A6. A7, A8, A9, A12,-   R¹ is more preferably (C₁-C₄)alkyl, (C₁-C₄)hydroxyalkyl,    (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,    (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₃-C₆)cycloalkyl,    (C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl or    (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,-   R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are more preferably    independently hydrogen, cyano, halogen, nitro, hydroxyl, amino, SCN,    tri-(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,    (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,    (C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkylhydroxyimino,    (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,    (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,    (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,    (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,    (C₁-C₄)alkylsulfonylamino. (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,    aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,    di-(C₁-C₄)alkylaminosulfonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino).    -   and also more preferably are phenyl or hetaryl, each of which is        optionally mono- or disubstituted identically or differently,        where (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, halogen, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, halo(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,        (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl,        (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl,        (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylhydroxyimino,        (C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino,        (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,        (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,        (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,        (C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino,        di-(C₁-C₄)alkylamino, aminosulfonyl, (C₁-C₄)alkylaminosulfonyl,        di-(C₁-C₄)alkylaminosulfonyl, NHCO—(C₁-C₄)alkyl        ((C₁-C₄)alkylcarbonylamino),-   Q is more preferably a heteroaromatic 9-membered or 12-membered    fused bicyclic or tricyclic ring system from the group of Q1 to Q20,

-   R⁴ is more preferably (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl (C₁-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl or    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,-   R⁵, R⁶ are independently more preferably hydrogen, cyano, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylsulfinyl,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyloxy,    (C₁-C₄)-alkylcarbonyl, (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,    (C₁-C₄)-alkylsulfonylamino, (C₁-C₄)-alkylamino,    di-(C₁-C₄)-alkylamino, aminosulfonyl, (C₁-C₄)-alkylaminosulfonyl or    di-(C₁-C₄)-alkylaminosulfonyl,-   n is more preferably 0, 1 or 2,-   m is more preferably 0, 1 or 2.

Configuration 4-1

-   Aa is even more preferably —S(O)_(m)—, —O—, or —C(R⁸)(R⁹)—,-   Ab is even more preferably —S(O)_(m)—, —O—, or —C(R¹⁰)(R¹¹)—,-   Ac is even more preferably —C(R¹²)(R¹¹)—,-   Ad is even more preferably —O— or —C(R¹⁴)(R¹⁵)—,    where not more than two of the Aa, Ab and Ad substituents at the    same time can be —O— or-   —S(O)_(m)—,    even more preferably resulting in the following structural units:    A1, A4, A6, A7, A8, A9,-   R¹ is even more preferably methyl, ethyl, n-propyl, isopropyl,    cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are even more preferably    independently hydrogen, cyano, halogen, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl,    (C₁-C₄)haloalkylsulfonyl or NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino).-   R⁷ is even more preferably (C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,-   Q is even more preferably a heteroaromatic 9-membered or 12-membered    fused bicyclic or tricyclic ring system from the group of Q2, Q3.    Q5. Q6, Q8, Q9, Q10, Q11. Q14, Q15. Q16, Q19 or Q20,

-   R⁴ is even more preferably (C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    -   R⁵ is even more preferably hydrogen, cyano, halogen,        (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl,        (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₃-C₄)alkoxyimino, (C₃-C₄)alkylthio,        (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,        (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylcarbonyl,        (C₁-C₄)haloaklcarbonyl, (C₁-C₄)alkylaminocarbonyl,        di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,        (C₁-C₄)alkylaminosulfonyl or di-(C₁-C₄)alkylaminosulfonyl,-   R⁶ is even more preferably hydrogen,-   n is even more preferably 0, 1 or 2,-   m is even more preferably 0, 1 or 2.

Configuration 4-2

-   Aa is even more preferably —C(R⁸)(R⁹)— or carbonyl,-   Ab is even more preferably —C(R¹⁰)(R¹¹)—,-   Ac is even more preferably —C(R¹²)(R¹³)—,-   Ad is even more preferably —C(R¹⁴)(R¹⁵)—,    even more preferably resulting in the following structural units:    A1. A12,-   R¹ is even more preferably methyl, ethyl, n-propyl, isopropyl,    cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are even more preferably    independently hydrogen, cyano, halogen, (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl,    (C₁-C₄)haloalkylsulfonyl, NHCO—(C₁-C₄)alkyl    ((C₁-C₄)alkylcarbonylamino) or hydroxyl,-   Q is even more preferably a heteroaromatic 9-membered or 12-membered    fused bicyclic or tricyclic ring system from the group of Q1, Q2,    Q3, Q10, Q14, Q16, Q17, Q18, Q19 or Q20,-   R⁴ is even more preferably (C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,-   R⁵ is even more preferably hydrogen, cyano, halogen. (C₁-C₄)alkyl,    (C₁-C₄)haloalkyl, (C₃-C₆)cycloalkyl,    (C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino,    (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl,    (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, (C₁-C₄)alkylaminocarbonyl,    di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,    (C₁-C₄)alkylaminosulfonyl or di-(C₁-C₄)alkylaminosulfonyl,-   R⁶ is even more preferably hydrogen, (C₁-C₄)alkyl or    (C₁-C₄)haloalkyl,-   n is even more preferably 0, 1 or 2.

Configuration 5-1

-   Aa is particularly —S(O)_(m)—, —O—, or —C(R⁸)(R⁹)—,-   Ab is particularly —S(O)—, —O—, or —C(R¹⁰)(R¹¹)—,-   Ac is particularly —C(R¹²)(R¹³)—,-   Ad is particularly —O—, or —(R¹⁴)(R¹⁵)—,    where not more than two of the Aa, Ab and Ad substituents at the    same time can be —O— or-   —S(O)_(m)—,    particularly resulting in the following structural units: A1, A4,    A6, A7, A8, A9,-   R¹ is particularly methyl, ethyl, n-propyl, i-propyl or cyclopropyl,-   R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are particularly independently    hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, difluoromethyl, trifluoroethyl, methoxy or ethoxy,-   R⁷ is particularly methyl, ethyl, isopropyl, methoxymethyl or    methoxyethyl,-   Q is particularly a heteroaromatic 9-membered fused bicyclic ring    system from the group of Q2, Q3, Q10, Q14 or Q16,

-   R⁴ is particularly methyl, ethyl, isopropyl, methoxymethyl or    methoxyethyl,-   R⁵ is even more preferably fluorine, chlorine, bromine,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂,    CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl    (CH₂CF₃, CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy or trifluoromethylthio,-   R⁶ is particularly hydrogen.-   n is particularly 0, 1 or 2,-   m is particularly 0, 1 or 2.

Configuration 5-2

-   Aa is particularly —C(R⁸)(R⁹)— or carbonyl,-   Ab is particularly —C(R¹⁰)(R¹¹)—,-   Ac is particularly —C(R¹²)(R¹³)—,-   Ad is particularly —C(R¹⁴)(R¹⁵)—,    particularly resulting in the following structural units: A1, A12,-   R¹ is particularly methyl, ethyl, n-propyl, i-propyl, cyclopropyl,    2,2,2-trifluoroethyl or 1,1-difluoroethyl,-   R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are particularly independently    hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, difluoromethyl or trifluoroethyl,-   Q is particularly a heteroaromatic 9-membered fused bicyclic ring    system from the group of Q1, Q2. Q3, Q17 or Q18,-   R⁴ is particularly methyl, ethyl, isopropyl, methoxymethyl or    methoxyethyl.-   R⁵ is even more preferably fluorine, chlorine, bromine,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂,    CHFCH₃), difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl    (CH₂CF₃, CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂),    pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,    dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl    or trifluoromethylsulfonyl,-   R⁶ is particularly hydrogen, methyl, ethyl, n-propyl, i-propyl or    difluoromethyl,-   n is particularly 0, 1 or 2.

Configuration 6-1

-   Aa is especially —C(R(R⁹)—,-   Ab is especially —C(R¹⁰)(R¹¹)—,-   Ac is especially —C(R¹²)(R¹³)—,-   Ad is especially —C(R¹⁴)(R¹⁵)—,    especially resulting in the following structural unit: A1,-   R¹ is especially ethyl,-   R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are especially hydrogen,-   Q is especially a heteroaromatic 9-membered fused bicyclic ring    system from the group of Q3.-   R⁴ is especially methyl,-   R⁵ is especially trifluoromethyl,-   R⁶ is especially hydrogen.-   n is especially 0 or 2.

Configuration 6-2

-   Aa is especially —C(R⁸)(R⁹)— or carbonyl,-   Ab is especially —C(R¹²)(R¹³)—,-   Ac is especially —C(R¹²)(R¹³)—,-   Ad is especially —C(R¹⁴)(R¹⁵)—,    especially resulting in the following structural units: A1, A12,-   R¹ is especially ethyl, methyl or 2,2,2-trifluoroethyl (CH₂CF₃),-   R⁸ is especially hydrogen, methyl, fluorine, chlorine or    trifluoromethyl.-   R⁹ is especially hydrogen or hydroxyl,-   R¹⁰ is especially hydrogen, methyl or trifluoromethyl,-   R¹¹ is especially hydrogen or methyl,-   R¹² is especially hydrogen, methyl or trifluoromethyl,-   R¹³ is especially hydrogen,-   R¹⁴ and R¹⁵ are especially hydrogen,-   Q is especially a heteroaromatic 9-membered fused bicyclic ring    system from the group of Q1, Q2, Q3, Q17 or Q18,-   R⁴ is especially methyl,-   R⁵ is especially trifluoromethyl, pentafluoroethyl,    2,2,2-trifluoroethyl, trifluoromethoxy, trifluoromethylthio,    trifluoromethylsulfinyl or trifluoromethylsulfonyl.-   R⁶ is especially hydrogen, methyl, ethyl, i-propyl or difluoromethyl    (CHF₂),-   n is especially 0, 1 or 2.

Configuration 6-3

-   Aa, Ab, Ac, Ad, Q, R¹, R⁴, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴,    R¹⁵ and n have the definitions given in configuration 6-2,    where only a maximum of two of the R⁸, R⁹, R¹⁰, R¹¹, R¹²    substituents can be different from hydrogen.

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q, R¹, R⁴, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴,R¹⁵ and n have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3) and

-   Aa is —C(R⁸)(R⁹)—,-   Ab is —C(R¹⁰)(R¹¹)—,-   Ac is —C(R¹²)(R¹³)—,-   Ad is —C(R¹⁴)(R¹⁵)—,    resulting in the following structural unit: A1.

In a preferred embodiment, the invention relates to compounds of theformula (I) where R¹, R⁴, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵and n have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3) and

-   Aa is —C(R⁸)(R⁹)—,-   Ab is —C(R¹⁰)(R¹¹)—,-   Ac is —C(R¹²)(R¹³)—,-   Ad is —C(R¹⁴)(R¹⁵)—,    resulting in the following structural unit: A1

and Q is Q1.

In a preferred embodiment, the invention relates to compounds of theformula (I) where R¹, R⁴, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵and n have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3) and

-   Aa is —C(R⁸)(R⁹)—,-   Ab is —C(R¹⁰)(R¹¹)—,-   Ac is —C(R¹²)(R¹³)—,-   Ad is —C(R¹⁴)(R¹⁵)—,    resulting in the following structural unit: A1

and Q is Q2.

In a preferred embodiment, the invention relates to compounds of theformula (I) where R¹, R⁴, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵and n have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3) and

-   Aa is —C(R⁸)(R⁹)—,-   Ab is —C(R¹⁰)(R¹¹)—,-   Ac is —C(R¹²)(R¹³)—,-   Ad is —C(R¹⁴)(R¹⁵)—,    resulting in the following structural unit: A1

and Q is Q3.

In a preferred embodiment, the invention relates to compounds of theformula (I) where R¹, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and nhave the definitions described in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3) and

-   Aa is —C(R⁸)(R⁹)—,-   Ab is —C(R¹⁰)(R¹¹)—,-   Ac is —C(R¹²)(R¹³)—,-   Ad is —C(R¹⁴)(R¹⁵)—,    resulting in the following structural unit: A1

and Q is Q17.

In a preferred embodiment, the invention relates to compounds of theformula (I) where R¹, R⁵, R⁶, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and nhave the definitions described in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3) and

-   Aa is —C(R⁸)(R⁹)—,-   Ab is —C(R¹⁰)(R¹¹)—,-   Ac is —C(R¹²)(R¹³)—,-   Ad is —C(R¹⁴)(R¹⁵)—,    resulting in the following structural unit: A1-   and Q is Q18.

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q, R¹, R⁴, R⁵, R⁶, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and nhave the definitions described in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3) and

-   Aa is carbonyl.-   Ab is —C(R¹⁰)(R¹¹)—,-   Ac is —C(R¹²)(R¹³)—,-   Ad is —C(R¹⁴)(R¹⁵)—.    resulting in the following structural unit: A12.

In a preferred embodiment, the invention relates to compounds of theformula (I) where R¹, R⁴, R⁵, R⁶, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and nhave the definitions described in configuration (3-1) or configuration(3-2) or configuration (4-1) or configuration (4-2) or configuration(5-1) or configuration (5-2) or configuration (6-1) or configuration(6-2) or configuration (6-3) and

-   Aa is carbonyl,-   Ab is —C(R¹⁰)(R¹¹)—,-   Ac is —C(R¹²)(R¹³)—,-   Ad is —C(R¹⁴)(R¹⁵)—,    resulting in the following structural unit: A12

and Q is Q3.

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q1 and R⁶ is hydrogen

and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴,R¹⁵, n and m have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q2 and R⁶ is hydrogen

and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁷, R¹⁰, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴,R¹⁵, n and m have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q3 and R⁶ is hydrogen

and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴,R¹⁵, n and m have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q17 and R⁶ is hydrogen

and Aa, Ab, Ac, Ad, R¹, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, nand m have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q18 and R⁶ is hydrogen

and Aa, Ab, Ac, Ad, R¹, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, nand m have the definitions described in configuration (3-1) orconfiguration (3-2) or configuration (4-1) or configuration (4-2) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q1 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3), whereR⁵ is in the following position and R⁶ is hydrogen:

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q2 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3), whereR⁵ is in the following position and R⁶ is hydrogen:

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q3 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3), whereR⁵ and R⁶ are in the following positions:

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q17 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁷, R⁸, R⁹, R¹⁰,R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3), whereR⁵ is in the following position and R⁶ is hydrogen:

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q18 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁷, R⁸, R⁹, R¹⁰,R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3), whereR⁵ is in the following position and R⁶ is hydrogen:

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q1, Q2, Q17 or Q18 and Aa, Ab, Ac, Ad, R¹, R⁴,R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have thedefinitions described in configuration (3-1) or configuration (3-2) orconfiguration (4-1) or configuration (4-2) or configuration (5-1) orconfiguration (5-2) or configuration (6-1) or configuration (6-2) orconfiguration (6-3), where R⁶ is hydrogen.

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q1, Q2 or Q3 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitionsdescribed in configuration (3-1) or configuration (3-2) or configuration(4-1) or configuration (4-2) or configuration (5-1) or configuration(5-2) or configuration (6-1) or configuration (6-2) or configuration(6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q1 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions describedin configuration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q2 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions describedin configuration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q3 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions describedin configuration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q4 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q5 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q6 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q7 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q8 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q9 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q10 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q1 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q12 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q13 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q14 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q15 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q16 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions describedin configuration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q17 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q18 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q19 and Aa, Ab, Ac, Ad, R¹, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions describedin configuration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

In a preferred embodiment, the invention relates to compounds of theformula (I) where Q is Q20 and Aa, Ab, Ac, Ad, R¹, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, n and m have the definitions described inconfiguration (3-1) or configuration (3-2) or configuration (4-1) orconfiguration (4-2) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3).

With inclusion of structural units A1 to A12, this results in thefollowing principal structures of the formula (I):

where R¹, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, Q, m and n have themeanings given above.

The substituent Aa is identical to the substituent Aa; the substituentAb is identical to the substituent A_(b), the substituent Ac isidentical to the substituent A_(c), the substituent Ad is

identical to the substituent A_(d).

In the preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine.

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, benzyl, naphthyl, anthryl,phenanthrenyl, and is preferably in turn phenyl,

hetaryl (synonymous with heteroaryl, including as part of a larger unit,for example hetarylalkyl) is selected from the group of furyl, thienyl,pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl,pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl,1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl,benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl,benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl,benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl,cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl and indolizinyl,

heterocyclyl is a saturated 4-, 5- or 6-membered ring containing 1 or 2nitrogen atoms and/or one oxygen atom and/or one sulfur atom, forexample azetidinyl, pyrrolidinyl, piperidinyl, oxetanyl,tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, thietanyl,tetrahydrothiophenyl, tetrahydrothiopyranyl, piperazinyl, morpholinyland thiomorpholinyl.

In the particularly preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine.

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, benzyl, naphthyl, anthryl,phenanthrenyl, and is preferably in turn phenyl,

hetaryl (including as part of a larger unit, for example hetarylalkyl)is selected from the group consisting of pyridyl, pyrimidyl, pyrazinyl,pyridazinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl and tetrazolyl,heterocyclyl is selected from the group consisting of oxetanyl,tetrahydrofuryl and piperazinyl.

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Amongthese alkyl radicals, particular preference is given to C₁-C₆-alkylradicals. Special preference is given to C₁-C₄-alkyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl. Among these, preference is given to C₂-C₆-alkenylradicals and particular preference to C₂-C₄-alkenyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,I-propynyl and propargyl.

Among these, preference is given to C₃-C₆-alkynyl radicals andparticular preference to C₃-C₄-alkynyl radicals. The alkynyl radical mayalso contain at least one double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl. Among these, preference is given to C₃-C₆-cycloalkylradicals.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood in the present case to meanan O-alkyl radical, where the term “alkyl” is as defined above.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. Halogen here is fluorine, chlorine, bromine or iodine,especially fluorine, chlorine or bromine.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutionsmay be the same or different.

The radical definitions or illustrations given in general terms orlisted within ranges of preference apply correspondingly to end productsand to starting materials and intermediates. These radical definitionscan be combined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

Preference according to the invention is given to using compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to usingcompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to usingcompounds of the formula (I) which contain a combination of thedefinitions listed above as being very particularly preferred.

Most preference according to the invention is given to using compoundsof the formula (I) which contain a combination of the meanings listedabove as being most preferable.

Especially used according to the invention are compounds of the formula(I) which contain a combination of the meanings listed above as beingespecially emphasized.

Depending on the nature of the substituents, the compounds of theformula (I) may take the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. The invention therefore encompassespure stereoisomers and any desired mixtures of these isomers.

The inventive compounds of the formula (I) can be obtained by theprocesses shown in the following schemes:

Process A-1

The compounds of the formula (I) in which Q is Q1 to Q9 and Q19 can beprepared by known methods, for example analogously to the processesdescribed in WO2009/131237, WO2010/125985, WO2011/043404, WO2011/040629,WO2012/086848, WO2013/018928, WO2015/000715, WO2015/121136.PCT/EP2016/052122 or PCT/EP2016/052105.

The radicals R¹, R⁴, R⁵, R⁶, Aa, Ab, Ac, Ad and n have the definitionsdescribed above, A² and A³ are CH or N, A⁴ is O, S or N—R⁴ and X¹ ishalogen.

Step a)

The compounds of the formula (IV) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with carboxylic acids of the formula (III)in the presence of a condensing agent or a base.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257, WO2006/65703, WO2009/131237. WO2010/125985,WO2011/043404, WO2011/040629, WO2012/086848, WO2013/018928,WO2015/000715 or WO2016/091731.

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods. Possible preparation routes aredescribed in processes E to I.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (III) can be carried out neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, forexample pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at standard pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (V) can be prepared by condensing thecompounds of the formula (IV), for example analogously to the processesdescribed in WO2009/131237, WO2010/125985. WO2011/043404, WO2011/040629,WO2012/086848, WO2013/018928. WO2015/000715 or WO 2015/121136.

The conversion to compounds of the formula (V) can be carried out neator in a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be carried out in the presence of a condensing agent,an acid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulfonic acids such as para-toluenesulfonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

The compounds of the formula (I) where n is 0 can be prepared byreacting the compounds of the formula (V) with the compounds of theformula (VIa) in the presence of a base.

Mercaptan derivatives of the formula (VIa), for example methylmercaptan, ethyl mercaptan or isopropyl mercaptan, are eithercommercially available or can be prepared by known methods, for exampleanalogously to the processes described in US2006/25633. US2006/111591,U.S. Pat. No. 2,820,062, Chemical Communications, 13 (2000), 1163-1164or Journal of the American Chemical Society, 44 (1922), p. 1329.

The conversion to compounds of the formula (I) where n is 0 can becarried out neat or in a solvent, preference being given to conductingthe reaction in a solvent selected from customary solvents that areinert under the prevailing reaction conditions. Preference is given toethers, for example diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether, nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given here to caesium carbonate, sodiumcarbonate and potassium carbonate. Further suitable bases are alkalimetal hydrides, for example sodium hydride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

In the reaction described, X¹ is preferably a fluorine or chlorine atom.

Step d)

The compounds of the formula (I) where n is 1 can be prepared byoxidizing the compounds of the formula (I) where n is 0. The oxidationis generally carried out in a solvent selected from customary solventswhich are inert under the prevailing reaction conditions. Preference isgiven to halogenated hydrocarbons, for example dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene;alcohols such as methanol or ethanol; formic acid, acetic acid,propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide,meta-chloroperbenzoic acid or sodium periodate.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step e)

The compounds of the formula (I) where n is 2 can be prepared byoxidizing the compounds of the formula (I) where n is 1. The oxidationis generally carried out in a solvent. Preference is given tohalogenated hydrocarbons, for example dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols suchas methanol or ethanol; formic acid, acetic acid, propionic acid orwater.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step f)

The compounds of the formula (I) where n is 2 can also be prepared in aone-step process by oxidizing the compounds of the formula (I) where nis 0. The oxidation is generally carried out in a solvent.

Preference is given to halogenated hydrocarbons, for exampledichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene; alcohols such as methanol or ethanol; formic acid, aceticacid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Process A-2

The compounds of the formula (I) in which n is 2 and Q is Q1 to Q9 andQ19 can be prepared by known methods, for example analogously to theprocesses described in WO2009/131237, WO2010/125985, WO2011/043404,WO2011/040629, WO2012/086848, WO2013/018928, WO2015/000715 andWO2015/121136.

The R¹, R⁴, R⁵, R⁶, Aa, Ab, Ac, Ad, A² and A³ radicals have thedefinitions described above, A⁴ is O, S or N—R⁴, X¹ is halogen and M isan alkali metal (preferably sodium, potassium or lithium).

Step a)

Alternatively, compounds of the formula (II) where n is 2 can also beprepared in a one-step procedure, for example in analogy to the processdescribed in Journal of Organic Chemistry 2005, 70, 2696-2700 by ahalogen-sulfone exchange with a compound of the formula (VIb) proceedingfrom compounds of the formula (V). The exchange is generally carried outin a solvent. Preference is given to using polar aprotic solvents, forexample dimethyl sulfoxide and N,N-dimethylformamide.

Compounds of the formula (VIb) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in Organic Synthesis 1977, 57, 88-92; Tetrahedron Letters1979, 9, 821-824 and Bulletin de la Societe Chimique de France 1958, 4,447-450.

Examples of suitable sulfur reagents are the lithium, sodium orpotassium salts of sulfinic acid.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Process B

The compounds of the formula (I) in which Q represents Q10, Q11, Q14 orQ15 can be prepared by known methods, for example analogously to theprocesses described in US2009/203705, US2012/258951, WO2013/3298 or J.Med. Chem. 31, (1988) 1590-1595.

The radicals R¹, R⁵, R⁶, Aa, Ab, Ac, Ad and n have the definitionsdescribed above. A², A³, A⁴ and A⁵ are CH or N (where A², A³, A⁴ and A⁵are not all N) and X¹ is halogen.

Step a)

Carboxylic acids of the formula (III) are converted in analogy to theprocess described in WO2015/107117, WO2011/75643 or EP2671582 in thepresence of O,N-dimethylhydroxylamine hydrochloride to Weinreb amides ofthe formula (VI).

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods. Possible preparation routes aredescribed in processes E to I.

Step b, c)

Compounds of the formula (VI) can then be converted by known methods,for example in analogy to the process described in WO2011/75643, with aGrignard reagent, for example methylmagnesium bromide, to ketones of theformula (VII). Compounds of the formula (VIII) are obtainable bysubsequent halogenation analogously, for example, to the known methoddescribed in US2012/302573.

Step d)

The compounds of the formula (X) can be prepared by cyclizing thecompounds of the formula (VIII) with amines of the formula (IX). Thecyclization is effected, for example, in ethanol, acetonitrile orN,N-dimethylformamide by known methods in analogy to the processesdescribed, for example, in WO2005/66177, WO2012/88411, WO2013/3298,US2009/203705, US2012/258951. WO2012/168733, WO2014/187762 or J. Med.Chem. 31 (1988) 1590-1595.

The compounds of the formula (IX) are commercially available.

Step e)

The compounds of the formula (I) where n is 0 can be prepared byreacting the compounds of the formula (X) with the compounds of theformula (Via) in the presence of a base. Mercaptan derivatives of theformula (VIa), for example methyl mercaptan, ethyl mercaptan orisopropyl mercaptan, are either commercially available or can beprepared by known methods, for example analogously to the processesdescribed in US2006/25633. US2006/111591, U.S. Pat. No. 2,820,062,Chemical Communications, 13 (2000), 1163-1164 or Journal of the AmericanChemical Society, 44 (1922), p. 1329.

Step f, g)

The compounds of the formula (I) where n is 1 can be prepared byoxidizing the compounds of the formula (I) where n is 0. The oxidationis carried out by known methods using a suitable oxidizing agent, forexample hydrogen peroxide, meta-chloroperbenzoic acid or sodiumperiodate.

The compounds of the formula (I) where n is 2 can be prepared byoxidizing the compounds of the formula (I) where n is 1.

The oxidation is generally carried out in a solvent. Preference is givento halogenated hydrocarbons, for example dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols suchas methanol or ethanol; formic acid, acetic acid, propionic acid orwater. Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

Step h)

The compounds of the formula (I) where n is 2 can also be prepared in aone-step process by oxidizing the compounds of the formula (I) where nis 0. The oxidation is generally carried out in a solvent. Preference isgiven to halogenated hydrocarbons, for example dichloromethane,chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene;alcohols such as methanol or ethanol; formic acid, acetic acid,propionic acid or water. Examples of suitable oxidizing agents arehydrogen peroxide and meta-chloroperbenzoic acid.

Process C

The compounds of the formula (I) in which Q is Q16 can be prepared byknown methods, for example analogously to the processes described inWO2014/142292.

The R⁴, R⁵, R⁶, Aa, Ab, Ac and Ad radicals have the definitionsdescribed above. X¹ is halogen.

Step a)

The compounds of the formula (XI) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,374,646 or Bioorganic and MedicinalChemistry Letters 2003, 13, 1093-1096 by reacting compounds of theformula (III) with an ammonia source in the presence of a condensingagent.

Carboxylic acids of the formula (III) are either commercially availableor can be prepared by known methods. Possible preparation routes aredescribed in processes E to I.

In most cases, the ammonia source used is ammonium hydroxide.

The reaction of the compounds of the formula (III) with the ammoniasource is preferably carried out in a solvent selected from customarysolvents which are inert under the prevailing reaction conditions.Preference is given to ethers, for example dioxane or tetrahydrofuran.

A suitable condensing agent is, for example, carbonyldiimidazole.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure. Preferably, the reaction is carriedout at atmospheric pressure and temperatures from 20 to 70° C.

Step b)

The compounds of the formula (XIII) can be prepared in analogy to theprocess described in WO2014/142292 by reacting compounds of the formula(XI) with compounds of the formula (XII) in the presence of a palladiumcatalyst in basic media.

Compounds of the formula (XII) can be prepared, for example, analogouslyto the processes described in WO2014/142292. A palladium catalyst usedmay, for example, be[1,1′-bis-(diphenylphosphino)ferrocene]dichloropalladium(II).Frequently, the bases used are inorganic bases such as potassiumtert-butoxide.

The reaction is carried out in a solvent. Frequently, toluene is used.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure. Preferably, the reaction is carriedout at atmospheric pressure and temperatures from 20 to 110° C.

The further conversion of compounds of the formula (XIII) to compoundsof the formula (I) is carried out analogously to process A.

Process D-1

The compounds of the formula (I) in which Q represents Q12, Q13, Q17.Q18 or Q20 can be prepared by known methods, for example analogously tothe processes described in WO2010/91310, WO2012/66061 or WO2013/99041.

The R⁵, R⁶, Aa, Ab, Ac and Ad radicals have the definitions describedabove. A², A³ and A⁶ are CH or N (where A². A³ and A⁶ cannotsimultaneously be N). X¹ and X² are halogen.

Step a)

The compounds of the formula (XVI) can be prepared by reacting compoundsof the formula (XIV) with compounds of the formula (XV) under basicconditions, for example analogously to the processes described inWO2006/19831, WO2009/127686, Chem. Eur. J. 20 (2014), 974-978,WO2005/80388, WO2010/91310, WO2012/66061 or WO2013/99041.

Compounds of the formula (XIV) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in WO2005/100353, WO2012/66061 or in European Journal ofMedicinal Chemistry 45 (2010), 2214-2222.

Compounds of the formula (XV) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in WO2005/34943, Tetrahedron Lett. 56 (2015), 1096-1098,US2015/31540, US2008/4309, WO2005/103003, WO2011/97079, WO2005/9958,67529. WO2010/51781, WO2013/61305 or US2008/242685.

The bases used are usually inorganic bases such as sodium hydride,potassium carbonate or caesium carbonate.

The conversion to compounds of the formula (XVI) is usually carried outin a solvent, preferably in a nitrile, for example acetonitrile orpropionitrile, or in an aprotic polar solvent, for exampleN,N-dimethylformamide or N-methylpyrrolidone.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Alternatively, the reaction of compounds of the formula (XIV) withcompounds of the formula (XV) to give compounds of the formula (XVI) canalso be carried out by palladium-catalysed N-arylation, e.g. analogouslyto the processes described in Angewandte Chemie Int. Ed. 2011, 50,8944-8947.

The further conversion of compounds of the formula (XVI) to compounds ofthe formula (I) is carried out analogously to process A.

Process D-2

The compounds of the formula (I) in which Q is Q17. Q18 and Q20 can beprepared by known methods, for example analogously to the processesdescribed in WO2010/91310, WO2012/66061 or WO2013/99041, and by thegeneral processes detailed below.

The R⁵. R⁶, Aa, Ab, Ac and Ad radicals have the definitions describedabove. A² and A³ are CH or N. R¹⁶ is (C₁-C₄)-alkyl.

Step a)

The compounds of the formula (XXXVI) can be prepared by reactingcompounds of the formula (XXXIV) with compounds of the formula (XXXXV),for example in the presence of a Lewis acid such as Ti(i-OPr)₄, forexample analogously to the process described in Bioorganic & MedicinalChemistry Letters 27 (2017), 1593-1597.

Compounds of the formula (XXXXV) are either commercially available orcan be prepared analogously to the process described in WO2006/105971.Compounds of the formula (XXXIV) are likewise commercially available orcan be prepared analogously to the processes described in AngewandteChemie International Edition 50 (2011), 1702-1706 or Journal of theAmerican Chemical Society 133 (2011), 4702-4705.

Step b)

The esters of the formula (XXXVI) can be converted to the acid of theformula (XXXVII) by standard methods (cf. DE 2221647 and WO2011/41713),for example with an alkali metal hydroxide such as sodium hydroxide orlithium hydroxide as base in an alcohol as solvent, for example ethanolor methanol or a mixture of tetrahydrofuran and water.

Step c)

The compounds of the formula (XXXVIII) can be prepared by convertingcompounds of the formula (XXXVII) by means of iodolysis, as, forexample, in the processes described in Inorganic Chemistry 41 (2002),1339-1341 or WO2015/050379.

Step d)

The compounds of the formula (XXXIX) can be prepared by reacting thecompounds of the formula (XXXVIII) with the compounds of the formula(VIa) in the presence of a base. Mercaptan derivatives of the formula(VIa), for example methyl mercaptan, ethyl mercaptan or isopropylmercaptan, are either commercially available or can be prepared by knownmethods, for example analogously to the processes described inUS2006/25633, US2006/111591, U.S. Pat. No. 2,820,062, ChemicalCommunications, 13 (2000), 1163-1164 or Journal of the American ChemicalSociety, 44 (1922), p. 1329.

Step e)

The compounds of the formula (I) where n is 2 can be prepared byoxidation in a one-stage process. The oxidation is generally carried outin a solvent. Preference is given to halogenated hydrocarbons, forexample dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol orethanol; formic acid, acetic acid, propionic acid or water. Examples ofsuitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

Process E-1

Carboxylic acids of the formula (III) having the structural units A1,A2, A3 and A5 are either commercially available or can be prepared byknown methods, for example via condensation of aminohetaryl derivativeswith a suitable carbonyl compound and subsequent hydrogenation of thesix-membered ring analogously to the processes described in EuropeanJournal of Medicinal Chemistry, 29 (1994), 279-286; WO2006/71752;WO2012/80232; Journal of Medicinal Chemistry, 57 (2014), 4196-4212;WO2012/143599; WO2015/48245, WO2006/18725, Chemical Communications, 44(2010), 925-927; Journal of the American Chemical Society, 68 (1946),453-457; WO2009/29625; Journal of the American Chemical Society, 137(2015), 8388-8391; Journal of Medicinal Chemistry, 57 (2014), 4196-4212,Helvetica Chimica Acta, 55 (1972), 565-568, Synthesis, 9 (1985),884-886, DE 2221647, WO2011/41713 and WO2007/108750.

Aa is —N(R⁷)— or —C(R⁸)(R⁹)—, Ab is —N(R⁷)— or —C(R¹⁰)(R¹¹)—, Ac is—N(R⁷)— or —C(R¹²)(R¹³)— and Ad is —N(R⁷)— or —C(R¹⁴)(R¹⁵), where onlytwo of the Aa, Ab. Ac or Ad substituents at the same time can be—N(R⁷)—. R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴ and R¹⁵ are hydrogen, methyl,ethyl, propyl, trifluoromethyl, cyano or —COO—(C₁-C₄)-alkyl. X¹ ishalogen and R¹⁶ is (C₁-C₆)-alkyl. R⁷ is hydrogen.

Step a)

The compounds of the formula (XIX) can be prepared in analogy to theprocesses described in European Journal of Medicinal Chemistry, 29(1994) 279-286; WO2006/71752; WO2012/80232; Journal of MedicinalChemistry, 57 (2014), 4196-4212; WO2012/143599; WO2015/48245 andWO2006/18725 by reacting the compounds of the formula (XVII) with asuitable carbonyl compound, for example a bromopyruvate derivative ofthe formula (XVIII), at room temperature or under thermal conditions ina suitable solvent, for example ethanol, tetrahydrofuran, acetonitrileor dimethylformamide.

The bromopyruvate derivatives of the formula (XVIII) are commerciallyavailable. The compounds of the formula (XVII) are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in Chemical Communications, 44 (2010),925-927: Journal of the American Chemical Society, 68 (1946), 453-457;WO2009/29625; Journal of the American Chemical Society, 137 (2015),8388-8391; Journal of Medicinal Chemistry, 57 (2014), 4196-4212,Helvetica Chimica Acta, 55 (1972), 565-568 and Synthesis, 9 (1985),884-886.

Step b)

The compounds of the formula (XX) are either commercially available orcan be prepared in analogy to the processes described in WO2007/108750,Bioorganic & Medicinal Chemistry Letters, 25 (2015), 5115-5120,WO2015/067800, Journal of Medicinal Chemistry, 57 (2014), 3687-3706 andWO2012/019430 via hydrogenation of compounds of the formula (XIX).

Steps c) and d)

Compounds of the formula (XXI) can be prepared by known methods fromcompounds of the formula (XX) via halogenation in analogy to theprocesses described in WO2009/23179, WO2010/91411, WO2011/41713 andBioorganic and Medicinal Chemistry Letters, 22 (2012), 3460-3466, forexample with N-chlorosuccinimide as halogenating agent indimethylformamide as solvent.

The esters of the formula (XXI) can be converted to the acid of theformula (III) by standard methods (cf. DE 2221647 and WO2011/41713), forexample with an alkali metal hydroxide such as sodium hydroxide orlithium hydroxide as base in an alcohol as solvent, for example ethanolor a mixture of tetrahydrofuran and water.

Process E-2

Alternatively, the halogen X¹ can also be introduced into compounds ofthe formula (III) as well as a carboxylic acid, as, for example incompound (XXXIII). Compounds of the formula (XXXIII) can be obtained,for example, via hydrolysis of compounds of the formula (XX).

Step a)

The esters of the formula (XX) can be converted to the acid of theformula (XXXIII) by standard methods (cf. DE 2221647 and WO2011/41713),for example with an alkali metal hydroxide such as sodium hydroxide orlithium hydroxide as base in a solvent, for example ethanol or a mixtureof tetrahydrofuran and water.

Step b)

Compounds of the formula (III) can be prepared by known methods fromcompounds of the formula (XXXIII) via halogenation, for example inanalogy to the processes described in WO2009/23179, WO2010/91411,WO2011/41713 and Bioorganic and Medicinal Chemistry Letters, 22 (2012),3460-3466, for example with N-chlorosuccinimide or N-bromosuccinimide ashalogenating agent in a solvent, for example dimethylformamide oracetonitrile.

Process F

Carboxylic acids of the formula (III) having the structural units A1,A2, A3 and A5 are either commercially available or can be prepared byknown methods, for example analogously to the processes described inWO2012/038850, US2000/6046211, Journal of Medicinal Chemistry, 37(1994), 2774-2782, European Journal of Medicinal Chemistry, 29 (1994)279-286; WO2006/71752; WO2012/80232; Journal of Medicinal Chemistry, 57(2014), 4196-4212; WO2012/143599; WO2015/48245 and WO2006/18725.

-   Aa is —N(R⁷)— or —C(R⁸)(R⁹)—, Ab is —N(R⁷)— or —C(R¹⁰)(R¹¹)—, Ac is    —N(R⁷)— or —C(R¹²)(R¹³)— and Ad is —N(R⁷)— or —C(R¹⁴)(R¹⁵), where    only one substituent Aa, Ab, Ac or Ad can be —N(R⁷)—. R⁸, R⁹, R¹⁰,    R¹¹, R¹², R¹³, R¹⁴ and R¹⁵ are hydrogen, (C₁-C₄)-alkyl, —NH₂, —CO₂H,    O—(C₁-C₄)-alkyl or trifluoromethyl. R¹⁶ is (C₁-C₆)-alkyl. X¹ is    halogen.

Step a)

Compounds of the formula (XXII) can be prepared by known methods fromcompounds of the formula (XVII) in analogy to the processes described inWO2012/038850, US2000/6046211 and Journal of Medicinal Chemistry, 37(1994), 2774-2782 via hydrogenation of a 2-aminohetaryl compound.

Compounds of the formula (XVII) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in Chemical Communications, 44 (2010), 925-927; Journal of theAmerican Chemical Society, 68 (1946), 453-457; WO2009/29625; Journal ofthe American Chemical Society, 137 (2015), 8388-8391; Journal ofMedicinal Chemistry, 57 (2014), 4196-4212, Helvetica Chimica Acta, 55(1972), 565-568 and Synthesis, 9 (1985), 884-886.

The reaction is generally conducted in a solvent. Preference is given tousing alcohols, for example methanol, ethanol or isopropanol, or elsecarboxylic acids, for example acetic acid. Catalysts used may beheterogeneous systems composed, for example, of rhodium on carbon orplatinum dioxide.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step b)

Compounds of the formula (XX) can be converted to compounds of theformula (XIX) by known methods in analogy to the processes described inEuropean Journal of Medicinal Chemistry, 29 (1994) 279-286;WO2006/71752; WO2012/80232; Journal of Medicinal Chemistry, 57 (2014),4196-4212; WO2012/143599; WO2015/48245 and WO2006/18725 by reacting thecompounds of the formula (XXII) with a suitable carbonyl compound, forexample a bromopyruvate derivative of the formula (XVIII), at roomtemperature or under thermal conditions in a suitable solvent, forexample ethanol, toluene, pyridine, tetrahydrofuran, acetonitrile ordimethylformamide.

The bromopyruvate derivatives are commercially available.

Steps c) and d)

Compounds of the formula (XXI) can be prepared by known methods fromcompounds of the formula (XX) via halogenation in analogy to theprocesses described in WO2009/23179, WO2010/91411, WO2011/41713 andBioorganic and Medicinal Chemistry Letters, 22 (2012), 3460-3466, forexample with N-chlorosuccinimide as halogenating agent indimethylformamide as solvent.

The esters of the formula (XXI) can be converted to the acid of theformula (III) by standard methods (cf. DE 2221647 and WO2011/41713), forexample with an alkali metal hydroxide such as sodium hydroxide orlithium hydroxide as base in an alcohol as solvent, for example ethanolor a mixture of tetrahydrofuran and water.

Process G

Carboxylic acids of the formula (III) having the structural units A1 toA11 are either commercially available or can be prepared by knownmethods, for example analogously to the processes described in OrganicLetters, 14 (2012), 440-443, WO2012/104415, Journal of OrganicChemistry, 65 (2000), 8093-8095, Tetrahedron, 65 (2009), 2484-2496,Tetrahedron Letters, 49 (2008), 6313-6319, US2000/6046211, EuropeanJournal of Medicinal Chemistry, 18 (1983), 277-285, WO2014/167084,WO2006/130588, WO2008/103351, WO2003/093279, WO2001/053262 and Journalof Medicinal Chemistry, 49 (2006), 4623-4637.

Aa, Ab, Ac, Ad, Ae have the definitions described above, preferablygiving the structural units A1 to A11. The R⁷. R⁸, R⁹, R¹⁰, R¹¹, R¹²,R¹¹, R¹⁴ and R¹⁵ radicals have the definitions described above. R¹⁶ is(C₁-C₆)-alkyl. R¹⁷ is (C₁-C₆)-alkyl and benzyl. X¹ is halogen.

Step a)

Compounds of the formula (XXIV) are either commercially available or canbe prepared via a thionation in analogy to the processes described inOrganic Letters, 14 (2012), 440-443, WO2012/104415, Journal of OrganicChemistry, 65 (2000), 8093-8095 and Tetrahedron, 65 (2009), 2484-2496.

Compounds of the formula (XXIII) are either commercially available orcan be prepared by known methods, for example analogously to theprocesses described in Applied Catalysis 510 (2016), 125-133, CatalysisCommunications, 70 (2015), 6-11, Biotechnology Journal, 9 (2014),1322-1328, ChemCatChem, 7 (2015), 2313-2317, WO2014/210354, Tetrahedron,71 (2015), 6349-6353, Chemistry—A European Journal, 20 (2014), 8867-8871and Journal of Catalysis, 305 (2013), 191-203.

The conversion to compounds of the formula (XXIV) is generally conductedin a solvent. Preference is given to using apolar aromatic hydrocarbons,for example toluene, mesitylene, xylene or benzene. It is also possibleto use polar aprotic solvents, for example acetonitrile.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step b)

Compounds of the formula (XXV) are either commercially available or canbe synthesized via an alkylation of compounds of the formula (XXIV) inanalogy to the processes described in Tetrahedron Letters, 49 (2008),6313-6319, US2000/6046211, European Journal of Medicinal Chemistry, 18(1983), 277-285 and WO2014/167084.

The conversion to compounds of the formula (XXIV) is generally conductedin a solvent. Preference is given to polar halogenated hydrocarbons, forexample dichloromethane, chloroform and 1,2-dichloroethane. It is alsopossible to use polar aprotic hydrocarbons, for example tetrahydrofuran,dialkyl ethers and acetone.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

Compounds of the formula (XXII) are either commercially available or canbe synthesized in analogy to the processes described in WO2006/130588,WO2008/103351, WO2003/093279, WO2001/053262 and Journal of MedicinalChemistry, 49 (2006), 4623-4637, for example from compounds of theformula (XXV) using ammonium hydroxide or ammonium chloride forintroduction of the amine.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step d)

Compounds of the formula (XXVI) are either commercially available or canbe prepared via an O-alkylation of compounds of the formula (XXIII) inanalogy to the processes described in Tetrahedron Letters, 42 (2001),1773-1776, WO2010/068520, Beilstein Journal of Organic Chemistry, 9(2013), 1463-1471, Tetrahedron Letters, 48 (1979), 4671-4674, Journal ofMedicinal Chemistry, 59 (2016), 3018-3033 and Bioorganic & MedicinalChemistry Letters, 15 (2005), 4359-4362.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step e)

Compounds of the formula (XXII) are either commercially available or canbe synthesized via an amination of compounds of the formula (XXVI) inanalogy to the processes described in Journal of Medicinal Chemistry, 35(1992), 189-194, Journal of the American Chemical Society, 108 (1986),5997-6003, US2000/6046211, US1998/5854234 and WO2008/078196.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step f)

Compounds of the formula (XX) can be converted to compounds of theformula (XXI) by known methods in analogy to the processes described inEuropean Journal of Medicinal Chemistry, 29 (1994) 279-286;WO2006/71752; WO2012/80232; Journal of Medicinal Chemistry, 57 (2014),4196-4212; WO2012/143599; WO2015/48245 and WO2006/18725 by reacting thecompounds of the formula (XXII) with a suitable carbonyl compound, forexample a bromopyruvate derivative of the formula (XVIII), at roomtemperature or under thermal conditions in a suitable solvent, forexample ethanol, toluene, pyridine, tetrahydrofuran, acetonitrile ordimethylformamide.

Aminating reagents used may be ammonia, ammonium chloride andshort-chain monoalkylamines.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Suitable bromopyruvate derivatives of the formula (XVIII) arecommercially available.

Steps g) and h)

Compounds of the formula (XXI) can be prepared by known methods fromcompounds of the formula (XX) via halogenation in analogy to theprocesses described in WO2009/23179, WO2010/91411, WO2011/41713 andBioorganic and Medicinal Chemistry Letters, 22 (2012), 3460-3466, forexample with N-chlorosuccinimide as halogenating agent indimethylformamide as solvent.

The esters of the formula (XXI) can be converted to the acid of theformula (III) by standard methods (cf. DE 2221647 and WO2011/41713), forexample with an alkali metal hydroxide such as sodium hydroxide orlithium hydroxide as base in an alcohol as solvent, for example ethanolor a mixture of tetrahydrofuran and water.

Process H

Carboxylic acids of the formula (III) with the structural unit A6 areeither commercially available or can be prepared analogously to theprocesses described hereinafter.

Aa is —O—, Ab is —C(R¹⁰)(R¹¹)—. Ac is —C(R¹²)(R¹³)— and Ad is—C(R¹⁴)(R¹⁵)—, R¹⁶ is C₁-C₆-alkyl. X¹ and X³ are halogen. R¹⁰, R¹¹, R¹²,R¹³, R¹⁴ and R¹⁵ are hydrogen.

Step a)

Compounds of the formula (XXIX) are either commercially available or canbe synthesized via an N-alkylation of imidazole derivatives of theformula (XXVII) with alkyl halides of the formula (XXVIII) by knownmethods in analogy to the processes described in Medicinal ChemistryResearch, 24 (2015), 2986-2992 and Indian Journal of Chemistry, SectionB: Organic Chemistry Including Medicinal Chemistry, 23B (1984), 363-368.

Compounds of the formula (XXVII) are either commercially available orcan be synthesized in analogy to the methods described in HannengCaliao, 18 (2010), 1-3, Jingxi Huangong Zhongjianti, 39 (2009), 65-67,Journal of Heterocyclic Chemistry, 39 (2002), 141-147, Chemical Biology& Drug Design, 85 (2015), 79-90 and Chinese Journal of Chemistry, 31(2013), 1539-1545.

Compounds of the formula (XXVIII) are either commercially available orcan be obtained from the corresponding alcohols analogously to theprocesses described in Biochemistry, 55 (2016), 470-481, OrganicLetters, 17 (2015), 6046-6049, Journal of the American Chemical Society,137 (2015), 11574-11577 and Organic & Biomolecular Chemistry, 13 (2015),3866-3870.

Suitable solvents used may, for example, be alcohols, such as methanol,ethanol and isopropanol.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step b)

Compounds of the formula (XXX) are either commercially available or canbe synthesized via an intramolecular nucleophilic substitution fromcompounds of the formula (XXIX) in analogy to the processes described inMedicinal Chemistry Research, 24 (2015), 2986-2992, Science, 322 (2008),1392-1395, Journal of Medicinal Chemistry, 52 (2009), 1317-1328,WO2007/075872 and Advanced Synthesis & Catalysis, 349 (2007), 2136-2144.

Suitable solvents used may, for example, be chlorinated hydrocarbons,for example dichloromethane and chloroform. The catalyst used may, forexample, be pyridinium para-toluenesulfonate.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

Compounds of the formula (XXXI) are either commercially available or canbe synthesized via a reduction of nitro derivatives of the formula (XXX)in analogy to the methods described in Dalton Transactions, 44 (2015),17453-17461, WO2008/063671, WO2007/0155738, Journal of MedicinalChemistry, 57 (2014), 144-158 and WO2012/030944.

The reducing agents used may, for example, be hydrogen and hydrazine.The reduction is conducted in the presence of a catalyst, for example asystem composed of palladium or palladium hydroxide. Solvents used areprotic hydrocarbons, for example methanol, ethanol, acetic acid andwater, or else aprotic hydrocarbons, for example ethyl acetate, ormixtures of the above.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step d)

Compounds of the formula (XXXII) are either commercially available orcan be prepared from compounds of the formula (XXXI) via adiazotization, followed by an electrophilic substitution with iodine, inanalogy to the methods described in Tetrahedron, 67 (2011), 9509-9517and Bioorganic & Medicinal Chemistry Letters, 20 (2012), 5864-5883.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step e)

Compounds of the formula (XX) are either commercially available or canbe synthesized via a carbonylation from compounds of the formula (XXXII)in analogy to the processes described in JP2004/123550, WO2006/038100,WO2012/126901, Journal of Organic Chemistry, 57 (1992), 3776-3780 andHelvetica Chimica Acta, 86 (2003), 3482-3509.

Carbonylating agents used may, for example, be n-alkyl formates orcarbon monoxide. Catalysts used may, for example, be palladium andsuitable palladium(II)-phosphine complexes.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Steps f) and g)

Compounds of the formula (XXI) can be prepared by known methods fromcompounds of the formula (XX) via halogenation in analogy to theprocesses described in WO2009/23179, WO2010/91411, WO2011/41713 andBioorganic and Medicinal Chemistry Letters, 22 (2012), 3460-3466, forexample with N-chlorosuccinimide as halogenating agent indimethylformamide as solvent.

The esters of the formula (XXI) can be converted to the acid of theformula (III) by standard methods (cf. DE 2221647 and WO2011/41713), forexample with an alkali metal hydroxide such as sodium hydroxide orlithium hydroxide as base in an alcohol as solvent, for example ethanolor a mixture of tetrahydrofuran and water.

Process I

Carboxylic acids of the formula (III) with the structural units A2, A3and A5 are either commercially available or can be synthesizedanalogously to the processes described hereinafter.

Aa is C(R⁸)(R⁹)—, Ab is —N(R⁷)— or —C(R¹⁰)(R¹¹)—, Ac is —N(R⁷)— or—C(R¹²)(R¹³)— and Ad is —N(R⁷)— or —C(R¹⁴)(R¹⁵)—, where only two of theAb, Ac and Ad substituents at the same time can be —N(R⁷)—. R⁸, R⁹, R¹⁰,R¹¹, R¹². R¹³, R¹⁴ and R¹⁵ have the definitions described above. R¹⁶ is(C₁-C₆)-alkyl. X¹ is halogen.

In compounds of the formula (XXIa), the R⁷ radical is hydrogen. Incompounds of the formula (XXIb), the R⁷ radical is C₁-C₄-alkyl, acetylor propionyl.

Step a)

Compounds of the formula (XXIb) are either commercially available or canbe prepared via an N-alkylation or N-acylation from compounds of theformula (XXIa) in analogy to the processes described in WO2016/012477.Bioorganic & Medicinal Chemistry Letters, 26 (2016), 2237-2244,WO2016/044546, JP2016/027024, WO2015/086525, WO2015/018754,WO2013/074388 and Journal of Medicinal Chemistry, 55 (2012), 4244-4273.

Alkylating agents used may, for example, be alkyl halides in combinationwith a base. Suitable bases are tertiary amine bases, for exampleHünig's base. Suitable solvents are, for example, polar aprotic solventssuch as N,N-dimethylformamide.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step b)

The esters of the formula (XXIb) can be converted to the acid of theformula (III) using standard methods (cf. DE 2221647 or WO2011/41713),for example with an alkali metal hydroxide such as sodium hydroxide orlithium hydroxide as base in an alcohol as solvent, for example ethanolor a mixture of tetrahydrofuran and water.

Compounds of the formula (I) can be converted to other, more highlysubstituted compounds of the formula (I) via processes described in theliterature. The scheme which follows shows illustrative conversions.

Process J

The R¹, R⁵, R⁶, Ab, Ac and Ad radicals have the definitions describedabove, A² and A³ are CH or N. A⁴ is O, S or N—R⁴. The R⁸, R⁹ and Aaradicals have the definitions specified in the scheme above.

Step a)

Compounds of the formula (I) where R⁸ and R⁹ may be hydrogen can beconverted to compounds of the formula (I) in which R⁸ is, for example,fluorine, chlorine or hydroxyl and R⁹ is hydrogen. The aforementionedderivatives can be prepared either in analogy to or in accordance withthe processes described in the literature. Fluorinations can beconducted, for example, in analogy to the processes described in Organic& Biomolecular Chemistry, 13 (2015), 2890-2894. Further halogenationsand oxidations at the A_(a) position can be implemented, for example, inanalogy to the processes described in Advanced Synthesis & Catalysis,349 (2007), 861-864.

Process K

The R¹, R⁴, R⁵, Aa, Ab, Ac and Ad radicals have the definitionsdescribed above, A³ is CH or N, A⁴ is O, S or N—R⁴. The R⁶ radical hasthe definitions specified in the scheme above.

Step a)

Compounds of the formula (I) in which R⁶ is hydrogen can additionally befunctionalized in this position, for example via alkylations orhaloalkylations, in analogy to the processes described in Organic &Biomolecular Chemistry, 13 (2015), 2890-2894 and Angewandte ChemieInternational Edition, 53 (2014), 4802-4806, in order to obtaincompounds of the formula (I) in which R⁶ is, for example, C₁-C₄-alkyl orC₁-C₄-haloalkyl.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablycarried out in agriculture and forestry, and in material protection.This preferably excludes methods for surgical or therapeutic treatmentof the human or animal body and diagnostic methods carried out on thehuman or animal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, especially crop protection compositions.

In the context of the present application, the term “pesticide” in eachcase also always encompasses the term “crop protection composition”.

The compounds of the formula (I), given good plant tolerance, favourableendotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, especially nematodes and molluscs, which areencountered in agriculture, in horticulture, in animal husbandry, inaquatic cultures, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector.

In the context of the present patent application, the term “hygiene”should be understood to mean any and all measures, provisions andprocedures which have the aim of preventing diseases, especiallyinfection diseases, and which serve to protect the health of humans andanimals and/or protect the environment and/or maintain cleanliness.According to the invention, this especially includes measures forcleaning, disinfection and sterilization, for example of textiles orhard surfaces, especially surfaces made of glass, wood, cement,porcelain, ceramic, plastic or else metal(s), in order to ensure thatthese are free of hygiene pests and/or their secretions. The scope ofprotection of the invention in this regard preferably excludes surgicalor therapeutic treatment procedures to be applied to the human body orthe bodies of animals, and diagnostic procedures which are carried outon the human body or the bodies of animals.

The term “hygiene sector” covers all areas, technical fields andindustrial applications in which these hygiene measures, provisions andprocedures are important, for example with regard to hygiene inkitchens, bakeries, airports, bathrooms, swimming pools, departmentstores, hotels, hospitals, stables, animal keeping, etc.

The term “hygiene pest” should therefore be understood to mean one ormore animal pests whose presence in the hygiene sector is problematic,especially for reasons of health. A main aim is therefore that ofavoiding, or limiting to a minimum degree, the presence of hygiene pestsand/or the exposure to these in the hygiene sector. This can especiallybe achieved through the use of a pesticide which can be used both forprevention of infestation and for prevention of an existing infestation.It is also possible to use formulations which prevent or reduce exposureto pests. Hygiene pests include, for example, the organisms mentionedbelow.

The term “hygiene protection” thus covers all acts by which thesehygiene measures, provisions and procedures are maintained and/orimproved.

The compounds of the formula (I) can preferably be used as pesticides.They are active against normally sensitive and resistant species andalso against all or specific stages of development. The abovementionedpests include:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida, for example Acarus spp., e.g. Acarus siro, Aceria kuko,Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculus fockeui, Aculusschlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp.,Boophilus spp., Brevipalpus spp., e.g. Brevipalpus phoenicis, Bryobiagraminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp.,Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoidesfarinae, Dermacentor spp., Eotetranychus spp., e.g. Eotetranychushicoriae, Epitrimerus pyri, Eutetranychus spp., e.g. Eutetranychusbanksi, Eriophyes spp., e.g. Eriophyes pyri, Glycyphagus domesticus,Halotydeus destructor, Hemitarsonemus spp., e.g. Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., e.g. Oligonychus coffeae, Oligonychus coniferarum,Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus,Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi,Ornithodorus spp., Ornithonyssus spp., Panonychus spp., e.g. Panonychuscitri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., e.g. Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., e.g. Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;

from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;

from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis; from the class of the Diplopoda, forexample Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea, e.g. Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Loboptera decipiens, Neostylopygarhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g.Periplaneta americana, Periplaneta australasiae, Pycnoscelussurinamensis, Supella longipalpa;

from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasticaalni, Agriotes spp., for example Agriotes linneatus, Agriotes mancus,Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum,Anoplophora spp., Anthonomus spp., for example Anthonomus grundis,Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., for exampleAtomaria linearis, Attagenus spp., Baris caerulescens, Bruchidiusobtectus, Bruchus spp., for example Bruchus pisorum, Bruchus rufimanus,Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., for exampleCeutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchusrapae, Chaetocnema spp., for example Chaetocnema confinis, Chaetocnemadenticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp.,Cosmopolites spp., for example Cosmopolites sordidus, Costelytrazealundica, Ctenicera spp., Curculio spp., for example Curculio caryae,Curculio caryatrypes, Curculio obtusus, Curculio sayi, Cryptolestesferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp.,for example Diabrotica balteata, Diabrotica barberi, Diabroticaundecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata,Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocisspp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachnaspp., for example Epilachna borealis, Epilachna varivestis, Epitrixspp., for example Epitrix cucumeris, Epitrix fuscula, Epitrixhirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp.,Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychusarator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hyperapostica, Hypomeces squamosus, Hypothenemus spp., for exampleHypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens,Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae,Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp.,for example Leucoptera coffeella, Lissorhoptrus oryzophilus, Listronotus(=Hyperodes) spp., Lixus spp., Luperodes spp., Luperomorpha xanthodera,Lyctus spp., Megascelis spp., Melanotus spp., for example Melanotuslongulus oregonensis, Meligethes aeneus, Melolontha spp., for exampleMelolontha melolontha, Migdolus spp., Monochamus spp., Naupactusxanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus,Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae,Otiorhynchus spp., for example Otiorhynchus cribricollis, Otiorhynchusligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus,Otiorhynchus sulcatus, Oulema spp., for example Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Phyllophaga helleri, Phyllotreta spp., for example Phyllotretaarmoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotretastriolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus,Psylliodes spp., for example Psylliodes affnis, Psylliodeschrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis,Rhizopertha dominica, Rhynchophorus spp., Rhynchophorus ferrugineus,Rhynchophorus palmarum, Sinoxylon perforans, Sitophilus spp., forexample Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae,Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechusspp., for example Sternechus paludatus, Symphyletes spp., Tanymecusspp., for example Tanymecus dilaticollis, Tanymecus indicus, Tanymecuspalliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp.,for example Tribolium audax, Tribolium castaneum, Tribolium confusum,Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., forexample Zabrus tenebrioides;

from the order of the Dermaptera, for example Anisolabis maritime,Forficula auricularia, Labidura riparia;

from the order of the Diptera, for example Aedes spp., for example Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,for example Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleiaheraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopotaspp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp.,Hypoderma spp., Liriomyza spp., for example Liriomyza brassicae,Liriomyza huidobrensis, Liriomyza sativae, Lucilia spp., for exampleLucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp., for exampleMusca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit,Paratanytarsus spp., Paralauterborniella subcincta, Pegomya or Pegomyiaspp., for example Pegomya betae, Pegomya hyoscyami, Pegomya rubivora,Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platypareapoeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., forexample Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta,Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex, Toxotrypana curvicauda;

from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., e.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobusbarodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrascaspp., e.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., e.g. Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma piri, Aphis spp., e.g. Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., e.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani,Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae,Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae,Cacopsylla spp., e.g. Cacopsylla pyricola, Calligypona marginata,Capulinia spp., Carneocephala fulgida, Ceratovacuna lanigera,Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspistegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila,Coccomytilus halli, Coccus spp., e.g. Coccus hesperidum, Coccuslongulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis,Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodeschittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp.,Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., e.g.Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccusspp., Empoasca spp., e.g. Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., e.g.Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspisspp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodiscacoagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., e.g.Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., e.g. Lecanium corni (=Parthenolecaniumcorni), Lepidosaphes spp., e.g. Lepidosaphes ulmi, Lipaphis erysimi,Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., e.g.Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae,Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiellaspp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., e.g. Myzus ascalonicus, Myzus cerasi,Myzus ligustri, Myzus ornatus, Myzus persicae, Myzus nicotianae,Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g.Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra,Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxyachinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., e.g.Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., e.g. Pemphigusbursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp.,Phenacoccus spp., e.g. Phenacoccus madeirensis, Phloeomyzus passerinii,Phorodon humuli, Phylloxera spp., e.g. Phylloxera devastatrix,Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., e.g.Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis,Pseudaulacaspis pentagona, Pseudococcus spp., e.g. Pseudococcuscalceolariae, Pseudococcus comstocki, Pseudococcus longispinus,Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psyllaspp., e.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp.,Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., e.g.Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., e.g. Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., e.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta,Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidusarticulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., e.g. Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., e.g. Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Aelia spp., Anasatristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.,Campylomma livida, Cavelerius spp., Cimex spp., e.g. Cimex adjunctus,Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., e.g. Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp.,Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis,Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g.Lygocoris pabulinus, Lygus spp., e.g. Lygus elisus, Lygus hesperus,Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae,Monalonion atratum, Nezara spp., e.g. Nezara viridula, Nysius spp.,Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g.Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp.,Stephanitis nashi, Tibraca spp., Triatoma spp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespulaspp., Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g.Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema(Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp.,Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta,Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g.Vespa crabro, Wasmannia auropunctata, Xeris spp.;

from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber,

from the order of the Isoptera, for example Coptotermes spp., e.g.Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp.,Incisitermes spp., Kalotermes spp., Microtermes obesi, Nasutitermesspp., Odontotermes spp., Porotermes spp., Reticulitermes spp., e.g.Reticulitermes flavipes, Reticulitermes hesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., e.g. Adoxophyes orana, Aedialeucomelas, Agrotis spp., e.g. Agrotis segetum, Agrotis ipsilon, Alabamaspp., e.g. Alabama argillacea, Amyelois transitella, Anarsia spp.,Anticarsia spp., e.g. Anticarsia gemmatalis, Argyroploce spp.,Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara,Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoeciaspp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella,Carposina niponensis, Cheimatobia brumata, Chilo spp., e.g. Chiloplejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp.,Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp.,Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp.,Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. Cydia nigricana,Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp.,Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpuslignosellus, Eldana saccharina, Ephestia spp., e.g. Ephestia elutella,Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Erannis spp.,Erschoviella musculana, Etiella spp., Eudocima spp., Eulia spp.,Eupoecilia ambiguella, Euproctis spp., e.g. Euproctis chrysorrhoea,Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp.,Grapholitha spp., e.g. Grapholita molesta, Grapholita prunivora,Hedylepta spp., Helicoverpa spp., e.g. Helicoverpa armigera, Helicoverpazea, Heliothis spp., e.g. Heliothis virescens Hofmannophilapseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella,Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresiamolesta, Leucinodes orbonalis, Leucoptera spp., e.g. Leucopteracoffeella, Lithocolletis spp., e.g. Lithocolletis blancardella,Lithophane antennata, Lobesia spp., e.g. Lobesia botrana, Loxagrotisalbicosta, Lymantria spp., e.g. Lymantria dispar, Lyonetia spp., e.g.Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestrabrassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimnaseparata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisaspp., Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., e.g.Ostrinia nubilalis, Panolis flammea, Parnara spp., Pectinophora spp.,e.g. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp.,e.g. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycterspp., e.g. Phyllonorycter blancardella, Phyllonorycter crataegella,Pieris spp., e.g. Pieris rapae, Platynota stultana, Plodiainterpunctella, Plusia spp., Plutella xylostella (=Plutellamaculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletiaspp., e.g. Pseudaletia unipuncta, Pseudoplusia includens, Pyraustanubilalis, Rachiplusia nu, Schoenobius spp., e.g. Schoenobiusbipunctifer, Scirpophaga spp., e.g. Scirpophaga innotata, Scotiasegetum, Sesamia spp., e.g. Sesamia inferens, Sparganothis spp.,Spodoptera spp., e.g. Spodoptera eradiana, Spodoptera exigua, Spodopterafrugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp.,Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora,Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tineapellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella,Trichoplusia spp., for example Trichoplusia ni, Tryporyza incertulas,Tuta absoluta, Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., e.g. Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., e.g. Locusta migratoria,Melanoplus spp., e.g. Melanoplus devastator, Paratlanticus ussuriensis,Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example Ceratophyllus spp.,Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., e.g. Frankliniella fusca,Frankliniella occidentalis, Frankliniella schultzei, Frankliniellatritici, Frankliniella vaccinii, Frankliniella williamsi, Haplothripsspp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi,Thrips spp., e.g. Thrips palmi, Thrips tabaci;

from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., e.g.Scutigerella immaculata; pests from the phylum of the Mollusca, forexample from the class of the Bivalvia, e.g. Dreissena spp.;

and also from the class of the Gastropoda, for example Arion spp., e.g.Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g.Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomaceaspp., Succinea spp.;

plant pests from the phylum of the Nematoda, i.e. plant-parasiticnematodes, in particular Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.,Hoplolaimus spp., Longidorus spp., for example Longidorus africanus,Meloidogyne spp., for example Meloidogyne chitwoodi, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp.,Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp.,Paratrichodorus spp., for example Paratrichodorus minor, Paratylenchusspp., Pratylenchus spp., for example Pratylenchus penetrans,Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulciusspp., Radopholus spp., for example Radopholus citrophilus, Radopholussimilis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.,Subanguina spp., Trichodorus spp., for example Trichodorus obtusus,Trichodorus primitivus, Tylenchorhynchus spp., for exampleTylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulussemipenetrans, Xiphinema spp., for example Xiphinema index.

The compounds of the formula (I) can, as the case may be, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). They can, as the case may be, also be used as intermediatesor precursors for the synthesis of other active ingredients.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I).Optionally, the use forms comprise further pesticides and/or adjuvantswhich improve action, such as penetrants, e.g. vegetable oils, forexample rapeseed oil, sunflower oil, mineral oils, for example paraffinoils, alkyl esters of vegetable fatty acids, for example rapeseed oilmethyl ester or soya oil methyl ester, or alkanol alkoxylates and/orspreaders, for example alkylsiloxanes and/or salts, for example organicor inorganic ammonium or phosphonium salts, for example ammonium sulfateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulfosuccinate or hydroxypropylguar polymers and/or humectants,for example glycerol and/or fertilizers, for example ammonium-,potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further active agrochemical ingredients.

Preference is given to formulations or use forms comprising auxiliaries,for example extenders, solvents, spontaneity promoters, carriers,emulsifiers, dispersants, frost protection agents, biocides, thickenersand/or further auxiliaries, for example adjuvants. An adjuvant in thiscontext is a component which enhances the biological effect of theformulation, without the component itself having any biological effect.Examples of adjuvants are agents which promote retention, spreading,attachment to the leaf surface or penetration.

These formulations are produced in a known manner, for example by mixingthe compounds of the formula (I) with auxiliaries, for exampleextenders, solvents and/or solid carriers and/or other auxiliaries, forexample surfactants. The formulations are produced either in suitablefacilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed-dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the simple and substituted amines, amides,lactams (such as N-alkylpyrrolidones) and lactones, the sulfones andsulfoxides (such as dimethyl sulfoxide).

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Useful liquid solvents areessentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulfoxide, and alsowater.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, for example xylene, tolueneor alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, for example chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, for example cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, for examplemethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones, for example acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents, for exampledimethyl sulfoxide, and water.

In principle, it is possible to use all suitable carriers. Suitablecarriers include more particularly the following: e.g. ammonium saltsand natural, finely ground rocks, such as kaolins, aluminas, talc,chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, andsynthetic, finely ground rocks, such as highly disperse silica,aluminium oxide and natural or synthetic silicates, resins, waxes and/orsolid fertilizers. It is likewise possible to use mixtures of suchcarriers. Useful carriers for granules include: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepiolite,dolomite, and synthetic granules of inorganic and organic flours, andalso granules of organic material such as sawdust, paper, coconutshells, maize cobs and tobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable extenders or carriers are those which are gaseous atstandard temperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonicacid, polycondensates of ethylene oxide with fatty alcohols or withfatty acids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulfosuccinic esters, taurinederivatives (preferably alkyl taurates), phosphoric esters ofpolyethoxylated alcohols or phenols, fatty acid esters of polyols, andderivatives of the compounds containing sulfates, sulfonates andphosphates, for example alkylaryl polyglycol ethers, alkylsulfonates,alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite wasteliquors and methylcellulose. The presence of a surfactant isadvantageous if one of the compounds of the formula (I) and/or one ofthe inert carriers is insoluble in water and if the application takesplace in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom include dyes such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyessuch as alizarin dyes, azo dyes and metal phthalocyanine dyes, andnutrients and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Additional components which may be present are stabilizers, such as coldstabilizers, preservatives, antioxidants, light stabilizers, or otheragents which improve chemical and/or physical stability. Foam generatorsor antifoams may also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further auxiliaries may bemineral and vegetable oils.

It is possible if appropriate for still further auxiliaries to bepresent in the formulations and the use forms derived therefrom.Examples of such additives are fragrances, protective colloids, binders,adhesives, thickeners, thixotropic agents, penetrants, retentionpromoters, stabilizers, sequestrants, complexing agents, humectants,spreaders. In general, the compounds of the formula (I) can be combinedwith any solid or liquid additive commonly used for formulationpurposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulfosuccinate, or increaseviscoelasticity, for example hydroxypropylguar polymers.

Useful penetrants in the present context are all those substances whichare typically used to improve the penetration of active agrochemicalingredients into plants. Penetrants are defined in this context by theirability to penetrate from the (generally aqueous) application liquorand/or from the spray coating into the cuticle of the plant and hence toincrease the mobility of the active ingredients in the cuticle. Themethod described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulfate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I), more preferably between 0.01%and 95% by weight of the compound of the formula (I), most preferablybetween 0.5% and 90% by weight of the compound of the formula (I), basedon the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. Application is accomplishedin a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) can also be used in a mixture with oneor more suitable fungicides, bactericides, acaricides, molluscicides,nematicides, insecticides, microbiological agents, beneficial organisms,herbicides, fertilizers, bird repellents, phytotonics, sterilants,safeners, semiochemicals and/or plant growth regulators, in order thus,for example, to broaden the spectrum of action, prolong the period ofaction, enhance the rate of action, prevent repellency or preventevolution of resistance. In addition, active ingredient combinations ofthis kind can improve plant growth and/or tolerance to abiotic factors,for example high or low temperatures, to drought or to elevated watercontent or soil salinity. It is also possible to improve flowering andfruiting performance, optimize germination capacity and rootdevelopment, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessibility of the harvested products.

In addition, the compounds of the formula (I) may be present in amixture with other active ingredients or semiochemicals such asattractants and/or bird repellents and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used to improve plant properties, for example growth, yieldand quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or in the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case. All the mixing components mentioned, as the casemay be, may also form salts with suitable bases or acids if they arecapable of doing so on the basis of their functional groups.

Insecticides/Acaricides/Nematicides

The active ingredients specified here with their common names are knownand are described for example in “The Pesticide Manual”, 16th ed.,British Crop Protection Council 2012, or can be searched for on theInternet (e.g. http://www.alanwood.net/pesticides). The classificationis based on the IRAC Mode of Action Classification Scheme applicable atthe time of filing of this patent application.

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g.alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g.acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos,propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos,sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel blockers, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators, for example pyrethroids, e.g.acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin,bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin[(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer],esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin,momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin,pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethrin, tetramethrin [(1R) isomer], tralomethrin and transfluthrinor DDT or methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, forexample neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor or flupyradifurone.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, forexample spinosyns, e.g. spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, forexample avermectins/milbemycins, e.g. abamectin, emamectin benzoate,lepimectin and milbemectin.

(7) Juvenile hormone mimetics, for example juvenile hormone analogues,e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Miscellaneous non-specific (multisite) inhibitors, for example alkylhalides, e.g. methyl bromide and other alkyl halides; or chloropicrin orsulfuryl fluoride or borax or tartar emetic or methyl isocyanategenerator, e.g. diazomet and metam.

(9) Chordotonal organ modulators, e.g. pymetrozine or flonicamide.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect midgut membrane, for exampleBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis andB.t. plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A,mCry3A, Cry3Ab, Cry3Bb, Cry34 Ab1/35Ab1.

(12) Inhibitors of mitochondrial ATP synthase, such as ATP disruptors,for example diafenthiuron or organotin compounds, e.g. azocyclotin,cyhexatin and fenbutatin oxide or propargite or tetradifon.

(13) Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinic acetylcholine receptor channel blockers, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, for examplebistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

(17) Moulting disruptors (especially in the case of Diptera), forexample cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, for example amitraz.

(20) Mitochondrial complex III electron transport inhibitors, forexample hydramethylnon or acequinocyl or fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, for exampleMETI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, for example indoxacarbor metaflumizone.

(23) Inhibitors of acetyl CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors, for examplephosphines, e.g. aluminium phosphide, calcium phosphide, phosphine andzinc phosphide, or cyanides, calcium cyanide, potassium cyanide andsodium cyanide.

(25) Mitochondrial complex II electron transport inhibitors, for examplebeta-keto nitrile derivatives, e.g. cyenopyrafen and cyflumetofen andcarboxanilides, for example pyflubumide.

(28) Ryanodine receptor modulators, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,

further active ingredients, for example afidopyropen, afoxolaner,azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide,bromopropylate, chinomethionat, chloroprallethrin, cryolite,cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol,epsilon metofluthrin, epsilon momfluthrin, flometoquin,fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin,flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide,fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappabifenthrin, kappa tefluthrin, lotilaner, meperfluthrin, paichongding,pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,tioxazafen, thiofluoximate, triflumezopyrim and iodomethane;additionally preparations based on Bacillus firmus (I-1582, BioNeem,Votivo), and the following compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635) (CAS 885026-50-6),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457) (CAS 637360-23-7),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494) (CAS 872999-66-1),3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2010052161) (CAS 1225292-17-0),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarbonate (known from EP 2647626) (CAS-1440516-42-6),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160) (CAS 792914-58-0), PF1364 (known fromJP2010/018586) (CAS Reg.No. 1204776-60-2),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(known from WO2012/029672) (CAS 1363400-41-2),(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one(known from WO2013/144213) (CAS 1461743-15-6),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926) (CAS 1226889-14-0),5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide(known from CN103232431) (CAS 1449220-44-3),4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamideand4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide(known from WO 2013/050317 A1) (CAS 1332628-83-7),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide,(+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamideand(−)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide(known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1)(CAS 1477923-37-7),5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile(known from CN 101337937 A) (CAS 1105672-77-2),3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide,(Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO 2012/034403 A1) (CAS 1268277-22-0),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from WO 2011/085575 A1) (CAS 1233882-22-8),4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide(known from CN 101715774 A) (CAS 1232543-85-9); cyclopropanecarboxylicacid 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylester (known from CN 103524422 A) (CAS 1542271-46-4);(4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazole-3-yl]phenyl]carbamate]-α-L-mannopyranose(known from US 2014/0275503 A1) (CAS 1181213-14-8);8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 1253850-56-4),(8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 933798-27-7),(8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) andN-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide(known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9).

Fungicides

The active ingredients specified herein by their common name are knownand described, for example, in “Pesticide Manual” (16th Ed. British CropProtection Council) or searchable on the internet (for example:http://www.alanwood.net/esticides).

All the mixing components mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups. All the fungicidalmixing components mentioned in classes (1) to (15), as the case may be,may include tautomeric forms.

1) Ergosterol biosynthesis inhibitors, for example (1.001)cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004)fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007)fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010)imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013)metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016)prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019)pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022)tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025)triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol(1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.038)1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.044)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.047)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.048)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.049)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.051)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.058)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.059)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.060)5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.061)5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.062)5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.063)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.064)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.065)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.066)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.067)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.068)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.069)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.070)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.071)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(1.072)N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.073)N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.074)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(1.075)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(1.076)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.077)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.078)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.079)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.080)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide.

2) Inhibitors of the respiratory chain in complex I or II, for example(2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004)carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad,(2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam(anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimericenantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate1RS,4SR,9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate1RS,4SR,9RS and the anti-epimeric racemate 1RS,4SR,9SR), (2.014)isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam(syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019)pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.023)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.024)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.025)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.028)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.029)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-arboxamide,(2.030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.031)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-arboxamide,(2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine,(2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.037)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.038)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.039)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.041)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-arboxamide,(2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(2.046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-arboxamide,(2.047)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(2.049)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-arboxamide,(2.050)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.051)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-arboxamide,(2.052)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-arboxamide,(2.054)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.

3) Inhibitors of the respiratory chain in complex III, for example(3.001) ametoctradin, (3.002) amisuibrom, (3.003) azoxystrobin, (3.004)coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007)dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadon, (3.010)fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013)kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016)picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019)pyraoxystrobin, (3.020) trifloxystrobin (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.025)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (3.026)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.027)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide.

4) Mitosis and cell division inhibitors, for example (4.001)carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004)fluopicolid, (4.005) pencycuron, (4.006) thiabendazole, (4.007)thiophanate-methyl, (4.008) zoxamide, (4.009)3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(4.011)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine,(4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

5) Compounds having capacity for multisite activity, for example (5.001)Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004)chlorthalonil, (5.005) copper hydroxide, (5.006) copper naphthenate,(5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+)sulfate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013)mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017)copper oxine, (5.018) propineb, (5.019) sulfur and sulfur preparationsincluding calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022)ziram.

6) Compounds capable of triggering host defence, for example (6.001)acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004)tiadinil.

7) Amino acid and/or protein biosynthesis inhibitors, for example(7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycinhydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil,(7.006)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

(8) ATP production inhibitors, for example (8.001) silthiofam.

9) Cell wall synthesis inhibitors, for example (9.001) benthiavalicarb,(9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005)mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.009)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Lipid and membrane synthesis inhibitors, for example (10.001)propamocarb, (10.002) propamocarb hydrochloride, (10.003)tolclofos-methyl.

11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole,(11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl,(12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004)metalaxyl-M (mefenoxam).

13) Signal transduction inhibitors, for example (13.001) fludioxonil,(13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005)quinoxyfen, (13.006) vinclozolin.

14) Compounds that can act as uncouplers, for example (14.001)fluazinam, (14.002) meptyldinocap.

15) Further compounds, for example (15.001) abscisic acid, (15.002)benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone,(15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid,(15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil,(15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014)fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon,(15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021)oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024)pentachlorophenol and salts, (15.025) phosphonic acid and salts thereof,(15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone)(15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide,(15.031)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.032)1-{4-(4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-{4-(5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-{4-(5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-(5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate, (15.045) 2-phenylphenol and salts thereof, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.047)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.049)4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050)5-amino-1,3,4-thiadiazole-2-thiol, (15.051)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene 2-sulfonohydrazide,(15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate,(15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides especially include bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, especially B. cereus strain CNCM 1-1562 or Bacillus firmus,strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus,especially strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, especially strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421), Bacillus thuringiensis, especially B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai,especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are: Beauveria bassiana, in particular strain ATCC 74040,Coniothyrium minitans, in particular strain CON/M/91-8 (Accession No.DSM-9660), Lecanicillium spp., in particular strain HRO LEC 12,Lecanicillium lecanii (formerly known as Verticillium lecanii), inparticular strain KV01, Metarhizium anisopliae, in particular strain F52(DSM3884/ATCC 90448), Metschnikowia fructicola, in particular strainNRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), inparticular strain IFPC 200613, or strain Apopka 97 (Accession No. ATCC20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251(AGAL 89/030550), Talaromyces flavus, in particular strain V117b,Trichoderma atroviride, in particular strain SCI (Accession Number CBS122089), Trichoderma harzianum, in particular T. harzianum rifai T39(Accession Number CNCM 1-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Examplesinclude:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondereBurkholderia cepacia (ehemals bekannt als Pseudomonas cepacia),Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp.,Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus,Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolii,Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are: Allium sativum, Artemisia absinthium,azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus,Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas,Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoasaponin extract), pyrethrum/pyrethrins, Quassia amara, Quercus,Quillaja, Regalia, “Requiem™ Insecticide”, rotenone, ryania/ryanodine,Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon,Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceaeextract, especially oilseed rape powder or mustard powder.

Safener as Mixing Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugarbeet, sugar cane, tomatoes, bell peppers, cucumbers, melons, carrots,water melons, onions, lettuce, spinach, leeks, beans, Brassica oleracea(e.g. cabbage) and other vegetable species, cotton, tobacco, oilseedrape, and also fruit plants (the fruits being apples, pears, citrusfruits and grapes). Crop plants may be plants which can be obtained byconventional breeding and optimization methods or by biotechnologicaland genetic engineering methods or combinations of these methods,including the transgenic plants and including the plant cultivars whichare protectable or non-protectable by plant breeders' rights. Plantsshall be understood to mean all development stages such as seed,seedlings, young (immature) plants, up to and including mature plants.Plant parts shall be understood to mean all parts and organs of theplants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also roots, tubers and rhizomes. Plantparts also include harvested plants or harvested plant parts andvegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seeds.

The inventive treatment of the plants and parts of plants with thecompounds of the formula (I) is effected directly or by allowing thecompounds to act on the surroundings, the habitat or the storage spacethereof by the customary treatment methods, for example by dipping,spraying, evaporating, fogging, scattering, painting on, injecting, and,in the case of propagation material, especially in the case of seeds,also by applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. Particular preference is given in accordance with the inventionto treating plants of the respective commercially customary plantcultivars or those that are in use. Plant cultivars are understood tomean plants having new properties (“traits”) and which have beenobtained by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better capability for storage and/orprocessability of the harvested products. Further and particularlyemphasized examples of such properties are increased resistance of theplants to animal and microbial pests, such as insects, arachnids,nematodes, mites, slugs and snails, owing, for example, to toxins formedin the plants, in particular those formed in the plants by the geneticmaterial from Bacillus thuringiensis (for example by the genes CryIA(a),CryIA(b), CryIA(c), CryIIA, CryIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb andCryIF and also combinations thereof), and also increased resistance ofthe plants to phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certain activeherbicidal compounds, for example imidazolinones, sulfonylureas,glyphosate or phosphinothricin (for example the “PAT” gene). The geneswhich impart the desired properties (“traits”) in question may also bepresent in combinations with one another in the transgenic plants.Examples of transgenic plants mentioned include the important cropplants, such as cereals (wheat, rice, triticale, barley, rye, oats),maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes, peas andother types of vegetable, cotton, tobacco, oilseed rape and also fruitplants (the fruits being apples, pears, citrus fruits and grapevines),particular emphasis being given to maize, soya beans, wheat, rice,potatoes, cotton, sugar cane, tobacco and oilseed rape. Properties(“traits”) which are particularly emphasized are the increasedresistance of the plants to insects, arachnids, nematodes and slugs andsnails.

Crop Protection—Types of Treatment

The plants and plant parts are treated with the compounds of the formula(I) directly or by action on their surroundings, habitat or storagespace using customary treatment methods, for example by dipping,spraying, atomizing, irrigating, evaporating, dusting, fogging,broadcasting, foaming, painting, spreading-on, injecting, watering(drenching), drip irrigating and, in the case of propagation material,in particular in the case of seed, additionally by dry seed treatment,liquid seed treatment, slurry treatment, by incrusting, by coating withone or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application,meaning that the compounds of the formula (I) are applied to thefoliage, in which case the treatment frequency and the application rateshould be adjusted according to the level of infestation with the pestin question.

In the case of systemically active ingredients, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I)according to the invention are introduced in solid form (e.g. in theform of granules) into the locus of the plants. In the case of paddyrice crops, this can also be accomplished by metering the compound ofthe formula (I) in a solid application form (for example as granules)into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements.Nevertheless, the treatment of seed entails a series of problems whichcannot always be solved in a satisfactory manner. Thus, it is desirableto develop methods for protecting the seed and the germinating plantwhich dispense with, or at least reduce considerably, the additionalapplication of pesticides during storage, after sowing or afteremergence of the plants. It is additionally desirable to optimize theamount of active ingredient used so as to provide optimum protection forthe seed and the germinating plant from attack by animal pests, butwithout damage to the plant itself by the active ingredient used. Inparticular, methods for the treatment of seed should also take accountof the intrinsic insecticidal or nematicidal properties ofpest-resistant or -tolerant transgenic plants in order to achieveoptimal protection of the seed and also the germinating plant with aminimum expenditure on pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It further alsocomprises a method where the seed is treated at different times with acompound of the formula (I) and a mixing component.

The invention also relates to the use of the compounds of the formula(I) for the treatment of seed for protecting the seed and the resultingplant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) according to the invention for protectionfrom animal pests. The invention also relates to seed which has beentreated simultaneously with a compound of the formula (I) and a mixingcomponent. The invention further relates to seed which has been treatedat different times with a compound of the formula (I) and a mixingcomponent. In the case of seed which has been treated at different timeswith a compound of the formula (I) and a mixing component, theindividual substances may be present on the seed in different layers. Inthis case, the layers comprising a compound of the formula (I) andmixing components may optionally be separated by an intermediate layer.The invention also relates to seed in which a compound of the formula(I) and a mixing component have been applied as part of a coating or asa further layer or further layers in addition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages that occur when a compound of the formula (I) actssystemically is that the treatment of the seed protects not only theseed itself but also the plants resulting therefrom, after emergence,from animal pests. In this way, the immediate treatment of the crop atthe time of sowing or shortly thereafter can be dispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions of signalling technology, leading to bettercolonization by symbionts such as, for example, rhizobia, mycorrhizaeand/or endophytic bacteria or fungi, and/or to optimized nitrogenfixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. More particularly, this is the seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beets (for example sugar beets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya beans,cotton, canola, oilseed rape, vegetables and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for treatment of transgenic seed which comprisesat least one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which has been soaked, for example in water, untilit reaches a certain stage of the rice embryo (“pigeon breast stage”)which results in stimulation of germination and more uniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activeingredients which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed inthe form of a suitable formulation. Suitable formulations and processesfor seed treatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customaryseed-dressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) with customary additives, for examplecustomary extenders and solvents or diluents, dyes, wetting agents,dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins, and also water.

Dyes which may be present in the seed-dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical ingredients. Usable with preference are alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of active agrochemical ingredients. Nonionic or anionicdispersants or mixtures of nonionic or anionic dispersants can be usedwith preference. Suitable nonionic dispersants especially includeethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulfated derivatives thereof. Suitable anionic dispersants areespecially lignosulfonates, polyacrylic acid salts andarylsulfonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for the formulation of active agrochemical ingredients.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz-und Schädlingsbekämpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats and triticale, and also the seed of maize, rice, oilseed rape,peas, beans, cotton, sunflowers, soya beans and beets, or else a widevariety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or the use forms prepared therefromthrough the addition of water, all mixing units usable customarily forthe seed dressing are useful. Specifically, the procedure in seeddressing is to place the seed into a mixer in batchwise or continuousoperation, to add the particular desired amount of seed-dressingformulations, either as such or after prior dilution with water, and tomix until the formulation is distributed homogeneously on the seed. Ifappropriate, this is followed by a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasite”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects or acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable endotherm toxicity are suitable for controllingparasites which occur in animal breeding and animal husbandry inlivestock, breeding animals, zoo animals, laboratory animals,experimental animals and domestic animals. They are active against allor specific stages of development of the parasites.

Agricultural livestock include, for example, mammals, such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deerand especially cattle and pigs; or poultry such as turkeys, ducks, geeseand especially chickens; or fish or crustaceans, for example inaquaculture; or, as the case may be, insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds; reptiles, amphibians or aquarium fish.

In a specific embodiment, the compounds of the formula (I) areadministered to mammals.

In another specific embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds or particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalhusbandry is enabled and better animal well-being is achievable.

In relation to the field of animal health, the term “control” or“controlling” in the present context means that the compounds of theformula (I) are effective in reducing the incidence of the particularparasite in an animal infected with such parasites to an innocuousdegree. More specifically, “controlling” in the present context meansthat the compounds of the formula (I) kill the respective parasite,inhibit its growth, or inhibit its proliferation.

The arthropods include, for example, but are not limited to,

from the order of Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.;

from the order of Mallophagida and the suborders Amblycerina andIschnocerina, for example, Bovicola spp., Damalina spp., Felicola spp.;Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp.,Trinoton spp., Werneckiella spp;

from the order of Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Atylotus spp.,Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culexspp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp.,Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp.,Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Luciliaspp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp.,Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp.,Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanusspp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;

from the order of Siphonapterida, for example, Ceratophyllus spp.,Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;

from the order of heteropterida, for example, Cimex spp., Panstrongylusspp., Rhodnius spp., Triatoma spp.; and also nuisance and hygiene pestsfrom the order Blattarida.

In addition, in the case of the arthropods, mention should be made byway of example, without limitation, of the following Acari:

from the subclass of Acari (Acarina) and the order of Metastigmata, forexample from the family of Argasidae such as Argas spp., Ornithodorusspp., Otobius spp., from the family of Ixodidae such as Amblyomma spp.,Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp.,Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genusof multi-host ticks); from the order of Mesostigmata such as Dermanyssusspp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp.,Sternostoma spp., Tropilaelaps spp., Varroa spp.; from the order of theActinedida (Prostigmata), for example, Acarapis spp., Cheyletiella spp.,Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp.,Ornithocheyletia spp., Psorergates spp., Trombicula spp.; and from theorder of the Acaridida (Astigmata), for example, Acarus spp.,Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp.,Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp.,Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp.,Tyrophagus spp.

Examples of parasitic protozoa include, but are not limited to:Mastigophora (Flagellata), such as:

Metamonada: from the order of Diplomonadida, for example, Giardia spp.,Spironucleus spp.

Parabasala: from the order of Trichomonadida, for example, Histomonasspp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp.,Tritrichomonas spp.

Euglenozoa: from the order of Trypanosomatida, for example, Leishmaniaspp., Trypanosoma spp.

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example,Entamoeba spp., Centramoebidae, for example Acanthamoeba sp.,Euamoebidae, e.g. Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): e.g. Cryptosporidium spp.;from the order of Eimeriida, for example, Besnoitia spp., Cystoisosporaspp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp.,Sarcocystis spp., Toxoplasma spp.; from the order of Adeleida, forexample, Hepatozoon spp., Klossiella spp.; from the order ofHaemosporida, for example, Leucocytozoon spp., Plasmodium spp.; from theorder of Piroplasmida, for example, Babesia spp., Ciliophora spp.,Echinozoon spp., Theileria spp.; from the order of Vesibuliferida, forexample, Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidiumspp., Nosema spp., and also, for example, Myxozoa spp.

The helminths that are pathogenic to humans or animals include, forexample, Acanthocephala, nematodes, Pentastoma and Platyhelminthes (e.g.Monogenea, cestodes and trematodes).

Illustrative helminths include, but are not limited to: Monogenea: e.g.Dactylogyrus spp., Gyrodactylus spp., Microbothrium spp., Polystomaspp., Troglecephalus spp.;

Cestodes: from the order of Pseudophyllidea, for example: Bothridiumspp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp.,Ligula spp., Schistocephalus spp., Spirometra spp.

From the order of cyclophyllida, for example: Andyra spp., Anoplocephalaspp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp.,Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp.,Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp.,Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephalaspp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp.,Thysanosoma spp.

Trematodes: from the class of Digenea, for example: Austrobilharziaspp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchisspp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoeliumspp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp.,Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp.,Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp.,Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeumspp., Leucochloridium spp., Metagonimus spp., Metorchis spp.,Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Ornithobilharziaspp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.,Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp.,Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Nematodes: from the order of Trichinellida, for example: Capillariaspp., Trichinella spp., Trichomosoides spp., Trichuris spp.

From the order of Tylenchida, for example: Micronema spp.,Parastrangyloides spp., Strongyloides spp.

From the order of Rhabditina, for example: Aelurostrongylus spp.,Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonemaspp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp.,Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomumspp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp.,Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroidesspp., Globocephalus spp., Graphidium spp., Gyalocephalus spp.,Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagiaspp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirusspp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp.,Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.;Ornithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperiaspp., Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp.,Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp.,Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylusspp., Syngamus spp., Teladorsagia spp., Trichonema spp.,Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp.,Uncinaria spp.

From the order of Spirurida, for example: Acanthocheilonema spp.,Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculurisspp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp.,Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.;Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp.,Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loaspp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp.,Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp.,Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp.,Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp.,Toxascaris spp., Toxocara spp., Wuchereria spp.

Acanthocephala: from the order of Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order ofMoniliformida, for example: Moniliformis spp.

From the order of Polymorphida, for example: Filicollis spp.; from theorder of Echinorhynchida, for example Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal husbandry, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic, metaphylacticor therapeutic.

Thus, one embodiment of the present invention relates to the compoundsof the formula (I) for use as a medicament.

A further aspect relates to the compounds of the formula (I) for use asan antiendoparasitic agent.

A further specific aspect of the invention relates to the compounds ofthe formula (I) for use as an antithelminthic agent, especially for useas a nematicide, platyhelminthicide, acanthocephalicide orpentastomicide.

A further specific aspect of the invention relates to the compounds ofthe formula (I) for use as an antiprotozoic agent.

A further aspect relates to the compounds of the formula (I) for use asan antiectoparasitic agent, especially an arthropodicide, veryparticularly an insecticide or an acaricide.

Further aspects of the invention are veterinary medicine formulationscomprising an effective amount of at least one compound of the formula(I) and at least one of the following: a pharmaceutically acceptableexcipient (e.g. solid or liquid diluents), a pharmaceutically acceptableauxiliary (e.g. surfactants), especially a pharmaceutically acceptableexcipient used conventionally in veterinary medicine formulations and/ora pharmaceutically acceptable auxiliary conventionally used inveterinary medicine formulations.

A related aspect of the invention is a method for production of aveterinary medicine formulation as described here, which comprises thestep of mixing at least one compound of the formula (I) withpharmaceutically acceptable excipients and/or auxiliaries, especiallywith pharmaceutically acceptable excipients used conventionally inveterinary medicine formulations and/or auxiliaries used conventionallyin veterinary medicine formulations.

Another specific aspect of the invention is veterinary medicineformulations selected from the group of ectoparasiticidal andendoparasiticidal formulations, especially selected from the group ofanthelmintic, antiprotozoic and arthropodicidal formulations, veryparticularly selected from the group of nematicidal,platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidaland acaricidal formulations, according to the aspects mentioned, andmethods for production thereof.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof an effective amount of a compound of the formula (I) in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof a veterinary medicine formulation as defined here in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to the use of the compounds of the formula (I) inthe treatment of a parasite infection, especially an infection caused bya parasite selected from the group of the ectoparasites andendoparasites mentioned here, in an animal, especially a nonhumananimal.

In the present context of animal health or veterinary medicine, the term“treatment” includes prophylactic, metaphylactic and therapeutictreatment.

In a particular embodiment, in this way, mixtures of at least onecompound of the formula (I) with other active ingredients, especiallywith endo- and ectoparasiticides, are provided for the field ofveterinary medicine.

In the field of animal health, “mixture” means not just that two (ormore) different active ingredients are formulated in a commonformulation and are correspondingly employed together, but also relatesto products comprising formulations separated for each activeingredient. Accordingly, when more than two active ingredients are to beemployed, all active ingredients can be formulated in a commonformulation or all active ingredients can be formulated in separateformulations; likewise conceivable are mixed forms in which some of theactive ingredients are formulated together and some of the activeingredients are formulated separately. Separate formulations allow theseparate or successive application of the active ingredients inquestion.

The active ingredients specified here by their “common names” are knownand are described, for example, in the “Pesticide Manual” (see above) orcan be searched for on the Internet (e.g.:http://www.alanwood.net/pesticides).

Illustrative active ingredients from the group of the ectoparasiticidesas mixing components include, without any intention that this shouldconstitute a restriction, the insecticides and acaricides listed indetail above. Further usable active ingredients are listed below inaccordance with the abovementioned classification based on the currentIRAC Mode of Action Classification Scheme: (1) acetylcholinesterase(AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodiumchannel modulators; (4) nicotinic acetylcholine receptor (nAChR)competitive modulators; (5) nicotinic acetylcholine receptor (nAChR)allosteric modulators; (6) glutamate-gated chloride channel (GluCl)allosteric modulators; (7) juvenile hormone mimetics; (8) miscellaneousnon-specific (multi-site) inhibitors; (9) chordotonal organ modulators;(10) mite growth inhibitors; (12) inhibitors of mitochondrial ATPsynthase, such as ATP disruptors; (13) uncouplers of oxidativephosphorylation via disruption of the proton gradient; (14) nicotinicacetylcholine receptor channel blockers; (15) inhibitors of chitinbiosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1;(17) moulting disruptors (especially in Diptera); (18) ecdysone receptoragonists; (19) octopamine receptor agonists; (21) mitochondrial complexI electron transport inhibitors; (25) mitochondrial complex II electrontransport inhibitors; (20) mitochondrial complex III electron transportinhibitors; (22) voltage-dependent sodium channel blockers; (23)inhibitors of acetyl CoA carboxylase; (28) ryanodine receptormodulators; active ingredients having unknown or non-specific mechanismsof action, e.g. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate,chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionat,triarathene, clothiazoben, tetrasul, potassium oleate, petroleum,metoxadiazone, gossyplur, flutenzine, brompropylate, cryolite;

compounds from other classes, for example butacarb, dimetilan,cloethocarb, phosphocarb, pirimiphos(-ethyl), parathion(-ethyl),methacrifos, isopropyl o-salicylate, trichlorfon, sulprofos, propaphos,sebufos, pyridathion, prothoate, dichlofenthion, demeton-S-methylsulfone, isazofos, cyanofenphos, dialifos, carbophenothion, autathiofos,aromfenvinfos(-methyl), azinphos(-ethyl), chlorpyrifos(-ethyl),fosmethilan, iodofenphos, dioxabenzofos, formothion, fonofos,flupyrazofos, fensulfothion, etrimfos;

organochlorine compounds, for example camphechlor, lindane, heptachlor,or phenylpyrazoles, e.g. acetoprole, pyrafluprole, pyriprole,vaniliprole, sisapronil; or isoxazolines, e.g. sarolaner, afoxolaner,lotilaner, fluralaner,

pyrethroids, e.g. (cis-, trans-)metofluthrin, profluthrin, flufenprox,flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin,RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin,biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin,clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenatedhydrocarbon compounds (HCHs), neonicotinoids, e.g. nithiazine

dicloromezotiaz, triflumezopyrim

macrocyclic lactones, e.g. nemadectin, ivermectin, latidectin,moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate;milbemycin oxime

triprene, epofenonane, diofenolan;

biologicals, hormones or pheromones, for example natural products, e.g.thuringiensin, codlemone or neem components

dinitrophenols, e.g. dinocap, dinobuton, binapacryl;

benzoylureas, e.g. fluazuron, penfluron,

amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz

beehive varroa acaricides, for example organic acids, e.g. formic acid,oxalic acid.

Illustrative active ingredients from the group of the endoparasiticides,as mixing components, include, but are not limited to, activeanthelmintic ingredients and active antiprotozoic ingredients.

The active anthelmintic ingredients include but are not limited to thefollowing active nematicidal, trematicidal and/or cestocidal compounds:

from the class of the macrocyclic lactones, for example: eprinomectin,abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin,latidectin, milbemectin, ivermectin, emamectin, milbemycin;

from the class of the benzimidazoles and probenzimidazoles, for example:oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole,oxfendazole, netobimin, fenbendazole, febantel, thiabendazole,cyclobendazole, cambendazole, albendazole sulfoxide, albendazole,flubendazole;

from the class of the depsipeptides, preferably cyclic depsipeptides,especially 24-membered cyclic depsipeptides, for example: emodepside,PF1022A;

from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;

from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;

from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;

from the class of the aminoacetonitriles, for example: monepantel;

from the class of the paraherquamides, for example: paraherquamide,derquantel;

from the class of the salicylanilides, for example: tribromsalan,bromoxanide, brotianide, clioxanide, closantel, niclosamide,oxyclozanide, rafoxanide;

from the class of the substituted phenols, for example: nitroxynil,bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan;

from the class of the organophosphates, for example: trichlorfon,naphthalofos, dichlorvos/DDVP, crufomate, coumaphos, haloxon;

from the class of the piperazinones/quinolines, for example:praziquantel, epsiprantel;

from the class of the piperazines, for example: piperazine, hydroxyzine;

from the class of the tetracyclines, for example: tetracycline,chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline;

from various other classes, for example: bunamidine, niridazole,resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquin,mirasan, miracil, lucanthon, hycanthon, hetolin, emetin,diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium,amoscanate, clorsulon.

Active antiprotozoic ingredients include, but are not limited to, thefollowing active ingredients: from the class of the triazines, forexample: diclazuril, ponazuril, letrazuril, toltrazuril;

from the class of polyether ionophores, for example: monensin,salinomycin, maduramicin, narasin;

from the class of the macrocyclic lactones, for example: milbemycin,erythromycin;

from the class of the quinolones, for example: enrofloxacin,pradofloxacin;

from the class of the quinines, for example: chloroquine;

from the class of the pyrimidines, for example: pyrimethamine;

from the class of the sulfonamides, for example: sulfaquinoxaline,trimethoprim, sulfaclozin;

from the class of the thiamines, for example: amprolium;

from the class of the lincosamides, for example: clindamycin;

from the class of the carbanilides, for example: imidocarb;

from the class of the nitrofurans, for example: nifurtimox;

from the class of the quinazolinone alkaloids, for example:halofuginone;

from various other classes, for example: oxamniquin, paromomycin;

from the class of the vaccines or antigens from microorganisms, forexample: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimerianecatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeriaacervulina, Babesia canis vogeli, Leishmania infantum, Babesia caniscanis, Dictyocaulus viviparus.

All the mixing components mentioned, as the case may be, may also formsalts with suitable bases or acids if they are capable of doing so onthe basis of their functional groups.

Vector Control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) onto a host or after injection into a host (for example malariaparasites by mosquitoes).

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of other worms;    -   Aedes: yellow fever, dengue fever, further viral disorders,        filariasis;    -   Simuliidae: transmission of worms, especially Onchocerca        volvulus;    -   Psychodidae: transmission of leishmaniasis

2) Lice: skin infections, epidemic typhus;

3) Fleas: plague, endemic typhus, tapeworms;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterialdiseases;

5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, SaintLouis encephalitis, tick-borne encephalitis (TBE), Crimean-Congohaemorrhagic fever, borreliosis;

6) Ticks: borellioses such as Borrelia bungdorferi sensu lato., Borreliaduttoni, tick-borne encephalitis, Q fever (Coxiella burnetii),babesioses (Babesia canis canis), ehrlichiosis.

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, Psychodidae such as Phlebotomus, Lutzomyia,lice, fleas, flies, mites and ticks, which can transmit pathogens toanimals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, in forests,in gardens and in leisure facilities, and also in the protection ofmaterials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders of Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) take the formof a ready-to-use pesticide, meaning that they can be applied to thematerial in question without further modifications. Useful furtherinsecticides or fungicides especially include those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active ingredients, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic protection sector, in the hygiene protection sectorand in the protection of stored products, particularly for control ofinsects, arachnids, ticks and mites encountered in enclosed spaces, forexample dwellings, factory halls, offices, vehicle cabins, animalbreeding facilities. For controlling animal pests, the compounds of theformula (I) are used alone or in combination with other activeingredients and/or auxiliaries. They are preferably used in domesticinsecticide products. The compounds of the formula (I) are effectiveagainst sensitive and resistant species, and against all developmentalstages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

PREPARATION EXAMPLES2-(3-Ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(I-002)

To a solution of 200 mg of2-(3-ethylsulfanyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(0.52 mmol) in 5.0 ml of dichloromethane were added 99 μl of formic acid(2.62 mmol) and 321 μl of hydrogen peroxide (3.67 mmol). The resultantmixture was stirred at room temperature for 16 h. The reaction mixturewas washed with saturated sodium thiosulfate solution. The organic phasewas removed, dried over sodium sulfate and concentrated. The residue waspurified by column chromatography via preparative HPLC with awater/acetonitrile gradient as eluent.

logP (HCOOH): 1.97; MH⁺: 414; ¹H-NMR (400 MHz, CDCl₃) δ ppm: 8.91 (s,1H), 8.08 (s, 1H), 4.39 (t, 2H), 4.04 (s, 3H), 3.76 (q, 2H), 3.04 (t,H), 2.11 (m, 2H), 2.02 (m, 2H), 1.42 (t, 3H).

In an analogous manner to compound (I-002), compound (I-043) wasprepared:

2-(3-Ethylsulfonyl-8-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(I-043)

logP (HCOOH): 2.31; MH⁺: 428; ¹H-NMR (400 MHz, CDCl₃) δ ppm: 8.90 (s,1H), 8.08 (s, 1H), 4.54-4.50 (m, 1H), 4.25-4.18 (m, 1H), 4.04 (s, 3H),3.83-3.69 (m, 2H), 3.13-3.08 (m, 1H), 2.24-2.16 (m, 2H), 2.05-2.01 (m,1H), 1.67-1.63 (m, 2H), 1.49 (d, 3H), 1.41 (t, 3H).

2-(3-Ethylsulfanyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(I-001)

1.00 g of2-(3-chloro-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo-[4,5-c]pyridine(2.81 mmol) were dissolved in 10.0 ml of N,N-dimethylformamide, 0.95 gof sodium thioethanolate (11.2 mmol) was added to the solution. Themixture was then stirred at room temperature for 16 h, another 0.95 g ofsodium thioethanolate (11.2 mmol) was added and the mixture was stirredfor a further 16 h. The reaction mixture was diluted with a mixture ofcyclohexane/ethyl acetate, filtered through Celite and concentrated. Thecrude product was converted further without further purification.

logP (HCOOH): 2.37; MH⁺: 382; ¹H-NMR (400 MHz, DMSO-4) δ ppm: 9.10 (s,1H), 8.15 (s, 1H), 4.20 (s, 3H), 4.03 (t, 2H), 3.31 (d, 2H), 2.99 (q,2H), 2.01 (m, 2H), 1.93 (m, 2H), 0.98 (t, 3H).

2-(3-Chloro-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(V-001)

To 1.00 g of3-chloro-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid(4.98 mmol) and 0.733 g ofN3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (3.83 mmol) dissolvedin 20.0 ml of pyridine was added 0.735 g ofN-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.83mmol). The mixture obtained was then stirred at 120° C. for 9 h. Thereaction mixture was cooled to room temperature, diluted withacetonitrile and filtered. The filtrate was concentrated to dryness. Thesolids were stirred in dichloromethane and filtered, and the filtrate inturn was concentrated. Without further purification, the crude productwas converted to2-(3-ethylsulfanyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(I-1).

logP (HCOOH): 2.26; MH⁺: 356; ¹H-NMR (400 MHz, CDCl₃) δ ppm: 8.85 (s,1H), 8.81 (br, 1H), 8.28 (t, 1H), 8.12 (s, 1H), 7.83 (m, 1H), 4.29 (s,3H), 3.98 (t, 2H), 2.96 (t, 2H), 2.12 (m, 2H), 1.99 (m, 2H).

2-(3-Ethylsulfonyl-7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-c]pyridine(I-034)

200 mg of2-(3-bromo-7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-c]pyridine(0.37 mmol), 7.2 mg of copper(I) iodide (0.03 mmol), 10.4 mg of(L)-proline (0.07 mmol) and 440 mg of sodium ethanesulfinate (3.79 mmol)were introduced into an argon-flooded reaction vessel, and 5 ml of DMSOwere added. Subsequently, the mixture was diluted with ethyl acetate.The organic phase was washed with saturated aqueous NaCl solution,separated off and concentrated on a rotary evaporator. The crude productwas purified by means of preparative HPLC (MeCN/H₂O).

logP (HCOOH): 2.80; MH⁺: 478; ¹H-NMR (400 MHz, CDCl₃) δ ppm: 8.93 (s,1H), 8.10 (s, 1H), 4.63 (ddd, 1H), 4.19-4.13 (m, 1H), 4.04 (s, 3H),3.85-3.73 (m, 2H), 3.20-3.14 (m, 1H), 2.57 (dd, 1H), 2.18-2.15 (m, 2H),1.78-1.73 (m, 1H), 1.42 (t, 3H), 1.21 (d, 3H).

2-(3-Bromo-7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-c]pyridine(V-002)

500 mg of3-bromo-7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylicacid (1.93 mmol), 490 mg ofN3-methyl-6-(1,1,2,2,2-pentafluoroethyl)pyridine-3,4-diamine (1.93 mmol)and 370 mg EDCI*HCl (1.93 mmol) were dissolved in 10 ml of pyridine andstirred under argon at 120° C. for 16 h. Subsequently, 37 mg of4-toluenesulfonic acid monohydrate (0.19 mmol) were added and themixture was stirred at 120° C. for a further 16 h. After being cooleddown to room temperature, the mixture was diluted with acetonitrile andfiltered, and the filtrate was concentrated. After column chromatographyon silica gel (CH₂Cl₂/MeOH; 10:1), the title compound was obtained fromthe residue.

logP (HCOOH): 3.39; MH⁺: 464; ¹H-NMR (400 MHz, CDCl₃) δ ppm: 8.96 (s,1H), 8.15 (s, 1H), 4.38 (s, 3H), 4.15 (ddd, 1H), 3.87-3.80 (m, 1H), 3.09(dd, 1H), 2.51 (dd, 1H), 2.18-2.11 (m, 2H), 1.78-1.73 (m, 1H), 1.20 (d,3H).

3-Bromo-7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylicacid (III-001)

5.00 g of 7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylicacid (27.7 mmol) were dissolved in 100 ml of DMF, and 5.68 g ofN-bromosuccinimide (31.9 mmol) were added. The reaction mixture wasstirred at room temperature for 16 h and then concentrated on a rotaryevaporator. The crude material was purified by column chromatography onsilica gel (CH₂Cl₂/MeOH; 10:1) in order to separate off the succinimide.The product obtained was converted further without further purification.

logP (HCOOH): 0.27, MH⁺: 259; ¹H-NMR (400 MHz, DMSO-d₆) δ ppm: 4.10 (dd,1H), 3.89-3.82 (m, 1H), 3.03 (dd, 1H), 2.55-2.48 (m, 1H), 2.07 (br, d,2H), 1.71-1.66 (m, 1H), 1.08 (d, 3H). (N.B.: the proton of the —COOHgroup is not shown in the spectrum.)

2-(3-Ethysulfonyl-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(I-031)

120 mg of2-(3-bromo-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(0.25 mmol), 4.9 mg of copper(I) iodide (0.02 mmol), 7.0 mg of(L)-proline (0.05 mmol) and 296 mg of sodium ethanesulfinate (2.55 mmol)were introduced into an argon-flooded reaction vessel, and 5 ml of DMSOwere added. Subsequently, the mixture was diluted with ethyl acetate.The organic phase was washed with saturated aqueous NaCl solution,separated off and concentrated on a rotary evaporator. The crude productwas purified by means of preparative HPLC (MeCN/H₂O).

logP (HCOOH): 2.51; MH⁺: 442, ¹H-NMR (400 MHz, CDCl₃) δ ppm: 8.91 (s,1H), 8.08 (s, 1H), 4.39 (t, 2H), 4.04 (s, 3H), 3.79 (q, 2H), 2.81 (s,2H), 1.90 (t, 3H), 1.41 (t, 2H), 1.15 (s, 6H).

2-(3-Bromo-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(V-003)

300 mg of3-bromo-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine-2-carboxylicacid (1.09 mmol), 210 mg ofN3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine (1.09 mmol) and 211 mgof EDCI*HCl (1.09 mmol) were dissolved in 5 ml of pyridine and heated to120° C. for 8 h. After being cooled down to room temperature, themixture was diluted with acetonitrile and filtered, and the filtrate wasconcentrated. After column chromatography on silica gel (CH₂Cl₂/MeOH;10:1), the title compound was obtained from the residue.

logP (HCOOH): 3.03; MH⁺: 428; ¹H-NMR (400 MHz, CDCl₃) δ ppm: 8.84 (s,1H), 8.12 (s, 1H), 4.27 (s, 3H), 3.98 (t, 2H), 2.73 (s, 2H), 1.89 (t,2H), 1.13 (s, 6H).

3-Bromo-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine-2-carboxylicacid (III-002)

1.85 g of7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine-2-carboxylic acidhydrochloride (7.61 mmol) were dissolved in 30 ml of DMF, and 1.56 g ofN-bromosuccinimide (8.76 mmol) were added while cooling with ice. Thereaction mixture was then warmed up to room temperature and stirred for16 h. The mixture was concentrated and purified by column chromatographyon silica gel (CH₂Cl₂/MeOH; 10:1), giving the desired product.

logP (HCOOH): 0.67; MH⁺: 273; ¹H-NMR (400 MHz, DMSO-d) δ ppm: 3.93 (t,2H), 2.68 (s, 2H), 1.83 (t, 2H), 1.03 (s, 6H). (The —COOH proton is notshown in the spectrum.)

7,7-Dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine-2-carboxylic acidhydrochloride

A solution of 2.15 g of methyl7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine-2-carboxylate (10.3mmol) in 30% hydrochloric acid was refluxed for 2 h. The excesshydrochloric acid was then removed under reduced pressure and the solidsobtained were dried at 60° C. under reduced pressure.

¹H-NMR (400 MHz, DMSO-d₆) δ ppm: 14.50 (br s, 2H), 8.26 (s, 1H), 4.15(t, 2H), 2.80 (s, 2H), 1.82 (t, 2H), 1.04 (s, 6H).

Methyl 7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine-2-carboxylate

In an autoclave, 7.00 g of2-bromo-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine (30.6 mmol),3.10 g of triethylamine (30.6 mmol) and 200 mg of Pd(dppf)Cl₂ (0.273mmol) were dissolved in 100 ml of methanol. The reaction mixture wasthen stirred under CO pressure (20 atm) at 80° C. for 16 h. The solventwas then removed and the residue that remained was admixed with water.The mixture was extracted with ethyl acetate, and the combined organicphases were washed with saturated aqueous NaCl solution, dried overNa₂SO₄ and concentrated. The residue was purified by columnchromatography on silica gel (CH₂Cl₂/MeOH; 10:1), giving the desiredproduct.

2-Bromo-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine

To a solution of 12.0 g of2,3-dibromo-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine (39.0mmol) in 100 ml of THF were added dropwise, under argon at −80° C., 17.2ml of n-BuLi (43.0 mmol, 2.5 M in hexane). The mixture was then stirredat −80° C. for 1 h, before methanol was added dropwise. The mixture waswarmed up to room temperature and concentrated. The residue was purifiedby column chromatography on silica gel (hexane/MTBE; 10:1), giving thedesired product.

2,3-Dibromo-7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine

To 9.75 g of 7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine (64.9mmol) in 500 ml of dichloromethane were added 28.9 g of1-bromopyrrolidine-2,5-dione (162 mmol). The reaction mixture wasstirred at room temperature for 1.5 h and then concentrated. The residuewas dissolved in ethyl acetate, and the organic solution obtained waswashed with saturated aqueous NaCl solution, dried over Na₂SO₄ andconcentrated. The crude product was converted further without furtherpurification.

7,7-Dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine

68 g ofN-(2,2-dimethoxyethyl)-4,4-dimethyl-3,5-dihydro-2H-pyridin-6-amine (317mmol) were dissolved in 30% hydrochloric acid and refluxed for 8 h.After cooling to room temperature, the reaction mixture was adjusted topH 810 by adding aqueous K₂CO₃ solution. The mixture was then extractedwith dichloromethane, the combined organic phases were dried overNa₂SO₄, and the solvent was removed under reduced pressure. The crudeproduct was converted further without further purification.

N-(2,2-Dimethoxyethyl)-4,4-dimethyl-3,5-dihydro-2H-pyridin-6-amine

To a solution of 44.8 g of6-methoxy-4,4-dimethyl-3,5-dihydro-2H-pyridine (317 mmol) in 400 ml oftoluene were added 50.0 g of 2,2-dimethoxyethan-1-amine (476 mmol). Themixture obtained was refluxed for 8 h. Subsequently, the solvent wasremoved and the crude product was directly converted further to7,7-dimethyl-6,8-dihydro-5H-imidazo[1,2-a]pyridine.

6-Methoxy-4,4-dimethyl-3,5-dihydro-2H-pyridine

To 40.2 g of dimethyl sulfate (319 mmol) were added 40.5 g of4,4-dimethylpiperidin-2-one (319 mmol) in portions. The reaction mixturewas stirred at 60° C. for 16 h, cooled down to room temperature andadded cautiously to saturated aqueous K₂CO₃ solution that had beencooled to 0° C. The product was extracted with dichloromethane, and thecombined organic phases were dried over Na₂SO₄ and concentrated. Thecrude product was converted further without further purification.

3-Ethylsulfonyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-ol(I-024)

62 mg of2-(3-ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(0.15 mmol) and 40 mg of N-bromosuccinimide (0.22 mmol) were dissolvedin 1 ml of N,N-dimethylformamide. The reaction mixture was then stirredat 60° C. for 48 h. After cooling to room temperature, the mixture wasconcentrated and purified directly by means of preparative HPLC (eluent:acetonitrile/H₂O), to isolate the desired product.

logP (HCOOH): 1.6; MH⁺: 430; ¹H-NMR (400 MHz, DMSO-d₆) δ ppm: 9.21 (s,1H), 8.24 (s, 1H), 5.3 (br s, 1H), 4.83 (t, 1H), 4.40 (m, 1H), 4.19 (m,1H), 4.01 (s, 3H), 3.75 (q, 2H), 2.20 (m, 1H), 2.07 (m 1H), 1.95 (m,2H), 1.28 (t, 3H).

2-(3-Ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3,4-dimethyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(I-039)

90.1 mg of2-(3-ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(0.22 mmol) and 4.5 mg of 9-mesityl-10-methylacridinium perchlorate(0.011 mmol) were dissolved in 2 ml of acetonitrile and TFA (1:1). Thesolution obtained was degassed with nitrogen for 1 min. Subsequently,tert-butyl peracetate (50% in mineral oil) was added, the reactionvessel was closed and irradiation was effected with blue light (at about2-5 cm) (Kessil A160 WE tuna blue lamp). The crude product was purifiedby chromatography by means of preparative HPLC (acetonitrile/H₂O).

logP (HCOOH): 2.1; MH⁺: 428; ¹H-NMR (500 MHz, DMSO-d₆) δ ppm: 8.02 (s,1H), 4.29 (t, 2H), 4.07 (s, 3H), 3.67 (q, 2H), 3.01 (s, 3H), 2.95 (t,2H), 2.03 (m, 2H), 1.92 (m, 2H), 1.26 (t, 3H).

4-Ethyl-2-(3-ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(I-040)

The compound (I-040) can be synthesized in analogy to the processdescribed for (I-039).

logP (HCOOH): 2.51; MH⁺: 442; ¹H-NMR (500 MHz, DMSO-d₆) δ ppm: 8.03 (s,1H), 4.29 (t, 2H), 4.04 (s, 3H), 3.66 (m, 2H), 3.36 (m, 2H), 2.95 (t,2H), 2.03 (m, 2H), 1.93 (m, 2H), 1.36 (t, 3H), 1.25 (t, 3H).

2-[3-(Ethylsulfonyl)-8-fluoro-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(I-026)

2-(3-Ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo-[4,5-c]pyridine(55 mg, 0.13 mmol), K₂S₂O₈ (72 mg, 0.27 mmol) and Selectfluor (94 mg,0.27 mmol) were dissolved under argon in a mixture of acetonitrile (1.3ml) and water (1.3 ml). The reaction mixture was then stirred at 80° C.for 1.5 h. Subsequently, CH₂Cl₂ was added, the mixture was extracted andthe organic phase was separated off. The aqueous phase was extractedonce more with CH₂Cl₂ and the combined organic phases were concentratedon a rotary evaporator. The residue was purified by means of preparativeHPLC, giving the desired product in 95% purity.

logP (HCOOH): 2.11; MH⁺: 432; ¹H-NMR (400 MHz, 600 MHz, CD₃CN) δ ppm:9.03 (s, 1H), 8.10 (q, 1H), 5.72 (dt, 1H), 4.60 (m, 1H), 4.14 (m, 1H),3.99 (s, 3H), 3.71 (q, 2H), 3.30 (m, 4H), 1.33 (t, 3H).

4-(Difluoromethyl)-2-[3-(ethylsulfonyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(I-025)

A mixture of2-(3-ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine(50 mg, 0.12 mmol) and zinc difluoromethanesulfinate (858 mg, 2.9 mmol)was dissolved in CH₃CN (2 ml) under air, and then trifluoroacetic acid(28 μl, 0.36 mmol) was added to the mixture obtained, tert-Butylhydroperoxide (70 wt % in H₂O, 0.50 ml, 3.6 mmol) was added dropwise tothe reaction mixture with vigorous stirring, and the mixture was thenstirred at room temperature for a further 18 h. The suspension wasfiltered and the mother liquor was concentrated to about 1 ml. Theresidue was purified via preparative HPLC, giving the title compound(I-025).

logP (HCOOH): 2.80; MH⁺: 464; ¹H-NMR (400 MHz, 600 MHz, CD₃CN) δ ppm:8.27 (s, 1H), 7.14 (t, 1H), 4.29 (t, 2H), 4.03 (t, 3H), 3.53 (q, 2H),2.95 (t, 2H), 2.07 (m, 2H), 1.97 (m, 2H), 1.30 (t, 3H).

3-(Ethylsulfonyl)-2-[3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridin-2-yl]-6,7-dihydro-imidazo[1,2-a]pyridin-8(5H)-one(I-030) and2-[8-chloro-3-(ethylsulfonyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(I-027)

To a mixture of2-[3-(ethylsulfonyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine(0.26 mmol), iron(III) chloride hexahydrate (0.13 mmol) and pyridine(1.0 ml) was added dropwise, while stirring at room temperature, asolution of tert-butyl hydroperoxide in water (70%, 0.50 mmol). Thereaction mixture was stirred at RT overnight. Subsequently, a furtherportion of iron(III) chloride hexahydrate (0.13 mmol) and tert-butylhydroperoxide (0.76 mmol) were added, and the resulting mixture wasstirred for a further 24 h. The mixture was then diluted with CH₂Cl₂ (80ml) and washed with sodium thiosulfate solution (10% in water, 20 ml).The organic phase was removed, dried and concentrated. Furtherpurification was effected by means of preparative HPLC (Waters XBridgeC18 5μ 100×30 mm, acetonitrile/H₂O+0.1% ammonia), followed by furtherpurification by means of preparative HPLC (Waters XBridge C18 5μ 100×30mm, acetonitrile/H₂O+0.1% formic acid). This gave the two titlecompounds.

(I-030): MS (ESIpos): m/z=428 [M+H]⁺; ¹H-NMR (400 MHz, DMSO-d₆) δ ppm:9.24 (s, 1H), 8.26 (s, 1H), 4.60 (m, 2H), 4.02 (s, 3H), 3.88 (q, 2H),2.82 (m, 2H), 2.43 (m, 2H), 1.32 (t, 3H).

(I-027): MS (ESIpos): m/z=448 [M+H]⁺; ¹H-NMR (400 MHz, acetonitrile-d₃)δ ppm: 9.05 (s, 1H), 8.12 (s, 1H), 5.48 (m, 1H), 4.60 (m, 1H), 4.20 (m,1H), 4.00 (s, 3H), 3.76 (q, 2H), 2.20 (m, 4H), 1.36 (t, 3H).

2-(3-Ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-b]pyridine (I-044)

140 mg of2-(3-ethylsulfanyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo-[4,3-b]pyridine(0.38 mmol) were dissolved in 20 ml of dichloromethane, and 130 mg ofm-CPBA (0.76 mmol) were added to the solution obtained at 0° C. Thereaction mixture was stirred at room temperature for 16 h and thendiluted with dichloromethane. The organic phase was washed with aqueousNa₂S₂O₃ solution, dried over Na₂SO₄ and concentrated. The residue waspurified by means of preparative thin-layer chromatography on silica gel(pentane/ethyl acetate: 1:1), giving the desired product (I-044).

MS (ESIpos): m/z=400 [M+H]⁺; ¹H-NMR (400 MHz, DMSO-d₆) δ ppm: 9.25 (s,1H), 8.91 (d, 1H), 8.80 (s, 1H), 4.30-4.29 (m, 2H), 3.69-3.33 (m, 2H),2.95-2.92 (m, 2H), 2.04-2.00 (m, 2H), 1.94-1.92 (m, 2H), 1.27 (t, 3H).

2-(3-Ethylsulfanyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-b]pyridine

200 mg of2-(3-iodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-b]pyridine(0.46 mmol) were dissolved in 10 ml of 1,4-dioxane, and 290 mg of EtSH(4.70 mmol), 70 mg of Pd₂(dba)₃*CHCl₃ (0.07 mmol), 80 mg of Xantphos(0.14 mmol) and 140 mg of DIPEA (1.40 mmol) were added. The reactionmixture was stirred at 80° C. for 16 h and then quenched with water. Theproduct was extracted with ethyl acetate, and the combined organicphases were washed with saturated aqueous NaCl solution, dried overNa₂SO₄ and concentrated on a rotary evaporator. The crude material waspurified by means of column chromatography on silica gel (pentane/ethylacetate, 2:1). MS (ESIpos): m/z=368 [M+H]⁺.

2-(3-Iodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-b]pyridine

A solution of 1.10 g of iodine (4.30 mmol) in 10 ml of dichloromethanewas added dropwise to 380 mg of2-[6-(trifluoromethyl)pyrazolo[4,3-b]pyridin-2-yl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylicacid (1.10 mmol), during which the pH was simultaneously kept at 11.5 to12.5 by addition of aqueous 1.0 M NaOH solution. The reaction solutionwas then diluted with dichloromethane and washed with aqueous Na₂S₂O₃solution. The organic phase was washed with saturated aqueous NaClsolution, dried over Na₂SO₄ and concentrated. Without furtherpurification, the crude product was converted further to2-(3-ethylsulfanyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-b]pyridine.

MS (ESIpos): m/z=434 [M+H]⁺.

2-[6-(Trifluoromethyl)pyrazolo[4,3-b]pyridin-2-yl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylicacid

500 mg of ethyl2-[6-(trifluoromethyl)pyrazolo[4,3-b]pyridin-2-yl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylate(1.30 mmol) were added to a mixture of 110 mg of NaOH (2.80 mmol) inH₂O/MeOH (10/10 ml), which was stirred at room temperature for 16 h. Themixture obtained was then adjusted to pH 3 with conc. HCl. The desiredproduct precipitated out in solid form, and was filtered off and dried.

MS (ESIpos): m/z=352 [M+H]⁺.

Ethyl2-[6-(trifluoromethyl)pyrazolo[4,3-b]pyridin-2-yl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylate

To a solution of 1.90 g of ethyl2-amino-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylate (9.25mmol) in 15 ml of toluene were added 1.00 g of3-azido-5-(trifluoromethyl)pyridine-2-carbaldehyde (4.63 mmol) and 5.30g of Ti(Oi-Pr)₄ (18.65 mmol). The reaction mixture was heated first to50° C. for 4 h and then to 100° C. for 1 h. The mixture obtained wasquenched with water and the product was extracted with ethyl acetate.The organic phase was washed with saturated aqueous NaCl solution, driedover Na₂SO₄ and concentrated on a rotary evaporator. The residue waspurified by means of a silica gel column (ethyl acetate/petroleum ether;1:2), giving the desired product.

MS (ESIpos): m/z=380 [M+H]⁺; ¹H-NMR (400 MHz, DMSO-d₆) δ ppm: 9.22 (s,1H), 8.88 (d, 1H), 8.77 (s, 1H), 4.30 (t, 2H), 4.05 (q, 2H), 2.90 (t,2H), 2.02-2.00 (m, 2H), 1.92-1.91 (m, 2H), 0.86 (t, 3H).

Ethyl 2-amino-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylate wasprepared in analogy to the process described in WO2006/105971.3-Azido-5-(trifluoromethyl)pyridine-2-carbaldehyde is a compound knownin the literature and was prepared as described in WO2011/074658.

2-(3-Ethylsulfonyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine(I-045)

The title compound (I-045) was synthesized in analogy to compound(I-044).

MS (ESIpos): m/z=400 [M+H]⁺; ¹H-NMR (400 MHz, DMSO-d₆) δ ppm: 9.42 (s,1H), 9.22 (s, 1H), 8.25 (s, 1H), 4.28 (t, 2H), 3.65 (q 2H), 2.93 (t,2H), 2.03-2.02 (m, 2H), 1.93-1.91 (m, 2H), 1.25 (t, 3H).

The azido component(4-azido-5-(trifluoromethyl)piperidine-2-carbaldehyde) needed for thesynthesis was obtained from the corresponding chlorine compound by meansof nucleophilic aromatic substitution with NaN₃.

The logP values are measured according to EEC Directive 79/831 AnnexV.A8 by HPLC (high-performance liquid chromatography) on areversed-phase column (C18). Temperature: 55° C.

The LC-MS determination in the acidic range is effected at pH 2.7 with0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid)as eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.Called logP (HCOOH) in the table.

The LC-MS determination in the neutral range is effected at pH 7.8 with0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrileas eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.Called logP (neutral) in the table.

Calibration is effected using unbranched alkan-2-ones (having 3 to 16carbon atoms) with known logP values (logP values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR data of selected examples are listed either in conventional form(8 values, multiplet splitting, number of hydrogen atoms) or as NMR peaklists.

In each case, the solvent in which the NMR spectrum was recorded isstated.

NMR Peak List Method

The 1H-NMR data of selected examples are noted in the form of 1H-NMRpeak lists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets are listed. The pairs of δvalue-signal intensity numbers for different signal peaks are listedwith separation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of 1H NMR spectra we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra measured in DMSO. Therefore, thetetramethylsilane peak may but need not occur in NMR peak lists.

The lists of the 1H NMR peaks are similar to the conventional 1H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional 1H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds, whichlikewise form part of the subject-matter of the invention, and/or peaksof impurities.

In the reporting of compound signals in the delta range of solventsand/or water, our lists of 1H NMR peaks show the usual solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in identifyingreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in conventional 1H NMRinterpretation.

Further details of 1H NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

In analogy to the examples and according to the above-describedpreparation processes, the following compounds of the formula (I) can beobtained:

Example Structure I-001

I-002

I-003

I-004

I-005

I-006

I-007

I-008

I-009

I-010

I-011

I-012

I-013

I-014

I-015

I-016

I-017

I-018

I-019

I-020

I-021

I-022

I-023

I-024

I-025

I-026

I-027

I-028

I-029

I-030

I-031

I-032

I-033

I-034

I-035

I-036

I-037

I-038

I-039

I-040

I-041

I-042

I-043

I-044

I-045

I-001: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 9.1038(1.8); 8.3195(7.1);8.3179(8.6); 8.1460(2.0); 7.9541(0.4); 5.8212(0.4); 5.8073(0.4);4.2030(6.2); 4.0476(0.7); 4.0340(1.4); 4.0194(0.9); 3.3245(1.5);3.3011(1.5); 3.0069(0.8); 2.9963(1.0); 2.9884(2.6); 2.9843(2.8);2.9665(3.7); 2.9503(1.6); 2.8929(2.4); 2.8829(1.6); 2.8679(0.8);2.7335(1.9); 2.5031(23.5); 2.1850(1.2); 2.1673(2.1); 2.1494(1.3);2.0957(16.0); 2.0070(0.8); 1.9959(0.8); 1.9240(0.8); 1.9096(0.8);1.5013(0.3); 1.4843(1.1); 1.4666(1.6); 1.4491(1.0); 1.1860(0.4);1.1843(0.4); 1.1437(0.3); 1.1250(0.7); 1.1167(1.8); 1.0999(3.5);1.0983(3.7); 1.0815(1.9); 1.0799(1.9); 0.9859(2.1); 0.9679(4.1);0.9501(2.0); 0.8881(0.5); 0.0016(3.2); −0.0002(3.7) I-002: ¹H-NMR(400.0MHz, CDCl3): δ = 8.9329(0.8); 8.1066(0.9); 7.2861(7.7); 5.3212(1.2);4.4215(0.3); 4.4067(0.7); 4.3913(0.4); 4.0586(3.2); 3.7953(0.7);3.7764(0.7); 3.0809(0.4); 3.0644(0.7); 3.0488(0.3); 2.1334(0.4);2.1213(0.3); 2.0569(0.3); 2.0434(0.3); 1.6968(16.0); 1.4572(0.7);1.4387(1.5); 1.4201(0.7) I-003: ¹H-NMR(400.0 MHz, CDCl3): δ =8.9212(3.9); 8.0879(3.7); 7.2631(9.7); 4.8343(0.8); 4.8208(0.8);4.7990(0.9); 4.7856(0.9); 4.3280(0.9); 4.3034(1.0); 4.2931(0.9);4.2681(0.8); 4.0556(16.0); 3.9145(0.5); 3.8966(0.8); 3.8792(1.5);3.8608(1.7); 3.8424(1.7); 3.8240(1.5); 3.8066(0.8); 3.7887(0.5);3.3197(0.3); 3.3083(0.6); 3.2966(0.4); 3.2759(0.5); 3.2636(0.8);3.2519(0.5); 3.0888(0.4); 3.0733(0.5); 3.0627(0.5); 3.0457(0.8);3.0284(0.4); 3.0183(0.4); 3.0022(0.3); 2.9069(0.4); 2.8999(0.4);2.8871(0.5); 2.8735(0.4); 2.8670(0.4); 2.4332(0.4); 2.4260(0.5);2.4179(0.4); 2.4088(0.5); 2.3995(0.6); 2.3918(0.6); 2.3848(0.5);2.1424(0.3); 2.1300(0.6); 2.1228(0.4); 2.1155(0.6); 2.1091(0.4);2.1029(0.4); 2.0955(0.6); 2.0882(0.4); 2.0811(0.5); 2.0074(0.6);1.5938(11.9); 1.4541(3.6); 1.4355(7.5); 1.4170(3.5); −0.0001(8.7) I-004:¹H-NMR(400.0 MHz, CDCl3): δ = 8.9258(5.0); 8.0900(8.1); 7.2619(42.6);5.3004(0.9); 4.5137(0.4); 4.4777(2.2); 4.0758(16.0); 3.9980(0.5);3.9815(0.7); 3.9645(0.9); 3.9456(0.8); 3.9227(0.7); 3.8900(1.4);3.8736(1.5); 3.8599(1.3); 2.3621(1.6); 2.3401(2.0); 2.2441(0.6);2.2196(1.0); 2.2056(0.9); 2.1762(0.5); 2.0790(0.8); 1.6457(2.1);1.4609(3.1); 1.4445(5.9); 1.4281(3.0); 1.2544(1.0); −0.0002(0.7) I-005:¹H-NMR(400.0 MHz, CDCl3): δ = 8.8719(4.7); 8.1300(5.1); 7.2857(8.7);4.3669(0.8); 4.3608(0.8); 4.3534(0.7); 4.3339(0.9); 4.3278(1.0);4.3204(0.7); 4.2444(16.0); 3.8959(0.5); 3.8850(0.6); 3.8567(1.0);3.8358(0.6); 3.8239(0.5); 3.1644(0.8); 3.1530(0.9); 3.1219(1.0);3.1103(1.0); 3.0216(1.2); 3.0037(3.6); 2.9854(3.8); 2.9674(1.4);2.5763(0.9); 2.5503(1.0); 2.5340(0.8); 2.5084(0.9); 2.1908(1.0);2.1598(1.6); 1.8987(0.6); 1.7967(0.4); 1.7830(0.4); 1.7703(0.7);1.7631(0.7); 1.7567(0.8); 1.7357(0.7); 1.7233(0.6); 1.2283(7.9);1.2168(8.1); 1.2126(9.1); 1.1987(11.1); 1.1803(5.2) I-006: ¹H-NMR(400.0MHz, CDCl3): δ = 8.8877(1.6); 7.9840(2.1); 7.1928(16.0); 5.2311(1.8);4.5103(0.4); 4.4762(0.4); 4.2623(0.4); 4.2380(0.4); 3.9619(5.8);3.8616(0.4); 3.7548(0.4); 2.2627(0.9); 2.2163(1.0); 2.1890(0.7);1.9167(0.4); 1.8565(0.5); 1.8469(0.5); 1.4016(1.2); 1.3838(2.5);1.3662(1.2); −0.0002(0.7) I-007: ¹H-NMR(400.0 MHz, CDCl3): δ =8.9291(4.4); 8.0915(5.3); 8.0358(2.0); 7.2646(7.3); 5.3004(3.2);4.6502(0.7); 4.6433(0.7); 4.6357(0.6); 4.6149(0.8); 4.6085(0.8);4.6021(0.6); 4.1995(0.5); 4.1888(0.6); 4.1713(0.7); 4.1609(0.8);4.1381(0.5); 4.1260(0.4); 4.0341(16.0); 3.8098(0.4); 3.7925(0.8);3.7744(1.5); 3.7555(1.6); 3.7506(1.6); 3.7319(1.5); 3.7141(0.8);3.6963(0.4); 3.2071(0.7); 3.1958(0.8); 3.1637(0.9); 3.1525(0.9);2.6111(0.9); 2.5851(1.0); 2.5687(0.8); 2.5423(0.9); 2.1830(1.0);2.1504(1.5); 1.7799(0.6); 1.7672(0.6); 1.7453(0.6); 1.7328(0.5);1.4300(3.6); 1.4115(7.4); 1.3931(3.5); 1.2202(6.7); 1.2042(6.5) I-008:¹H-NMR(400.0 MHz, CDCl3): δ = 8.8553(6.1); 8.1165(7.7); 7.2644(27.7);5.3010(0.6); 4.3190(1.2); 4.2955(1.3); 4.2863(1.2); 4.2249(16.0);3.4933(0.3); 3.4562(1.0); 3.4276(1.4); 3.3993(0.9); 3.1372(0.8);3.0967(1.2); 3.0019(1.5); 2.9836(4.2); 2.9652(4.7); 2.9468(2.2);2.9174(1.0); 2.8905(0.6); 2.8741(0.4); 2.1793(1.0); 2.1244(1.1);2.0916(1.1); 1.7891(3.4); 1.6811(0.7); 1.6582(1.0); 1.6492(1.0);1.6312(1.0); 1.2184(9.4); 1.2023(14.2); 1.1841(11.1); 1.1658(5.3);−0.0004(0.5) I-009: ¹H-NMR(400.0 MHz, CDCl3): δ = 8.9133(5.0);8.0896(6.5); 7.2652(10.2); 4.6254(1.0); 4.6135(1.0); 4.5912(1.1);4.5798(1.1); 4.0382(16.0); 3.7947(1.0); 3.7757(3.0); 3.7583(2.7);3.7401(2.1); 3.7124(1.0); 3.1811(0.7); 3.1419(1.0); 3.1365(1.1);3.0082(0.6); 2.9926(0.7); 2.9808(0.7); 2.9644(1.0); 2.9487(0.5);2.9369(0.5); 2.9205(0.4); 2.2006(0.7); 2.1243(0.8); 2.0915(0.8);2.0453(0.4); 1.8118(2.1); 1.7098(0.4); 1.6961(0.4); 1.6804(0.7);1.6674(0.8); 1.6493(0.7); 1.6352(0.6); 1.4386(3.2); 1.4208(7.0);1.4027(3.2); 1.2589(0.3); 1.2140(8.3); 1.1977(8.1) I-010: ¹H-NMR(400.0MHz, CDCl3): δ = 8.8561(1.8); 8.0201(2.3); 7.1918(16.0); 4.7596(0.3);4.7254(0.4); 4.1543(0.4); 4.0005(4.6); 3.8124(0.3); 3.7886(0.3);3.3150(0.4); 3.3068(0.4); 3.0400(0.3); 3.0133(0.4); 2.4235(0.4);2.3896(0.4); 1.5218(4.2); 1.3605(2.0); 1.1856(0.4); 0.0173(0.9);0.0086(2.7); −0.0001(58.9); −0.0090(2.7); −0.0242(0.5); −0.0618(0.9);−0.0698(22.8); −0.0775(1.0) I-011: ¹H-NMR(601.6 MHz, CDCl3): δ =8.6977(2.0); 8.6956(2.0); 8.2815(1.8); 7.2620(6.2); 5.2977(9.9);4.4011(1.5); 4.3912(2.6); 4.3810(1.5); 4.0162(16.0); 3.8315(0.8);3.8191(2.8); 3.8068(2.8); 3.7945(0.9); 3.0529(1.4); 3.0422(2.8);3.0316(1.4); 2.1239(0.3); 2.1140(0.8); 2.1081(0.9); 2.1041(1.4);2.0948(1.1); 2.0848(0.5); 2.0393(0.5); 2.0290(1.3); 2.0189(1.2);2.0097(0.9); 1.4357(3.2); 1.4234(7.0); 1.4110(3.2); 0.0051(0.6);−0.0002(20.4); −0.0058(0.7) I-012: ¹H-NMR(601.6 MHz, CDCl3): δ =8.9396(3.4); 8.1137(3.8); 7.2609(10.6); 5.2978(0.8); 4.4008(1.8);4.3909(3.4); 4.3808(1.9); 4.0469(16.0); 3.8143(1.0); 3.8020(3.1);3.7896(3.1); 3.7773(1.0); 3.0541(1.5); 3.0433(3.0); 3.0329(1.6);2.1295(0.4); 2.1105(1.8); 2.1016(1.5); 2.0914(0.7); 2.0341(1.6);2.0243(1.6); 2.0153(1.2); 1.4369(3.5); 1.4246(7.6); 1.4124(3.5);0.0051(0.8); −0.0002(39.3); −0.0057(1.6) I-013: ¹H-NMR(601.6 MHz,CDCl3): δ = 8.9466(2.8); 8.1233(2.9); 7.2601(15.0); 5.2977(1.9);4.4118(1.6); 4.4017(3.0); 4.3915(1.6); 4.0700(16.0); 3.6207(14.4);3.0508(1.4); 3.0402(2.8); 3.0296(1.4); 2.3545(1.0); 2.1402(0.4);2.1307(0.9); 2.1252(1.0); 2.1205(1.6); 2.1112(1.2); 2.1009(0.6);2.0457(0.6); 2.0353(1.4); 2.0252(1.4); 2.0160(1.0); 2.0051(0.4);0.0052(1.5); −0.0002(53.9); −0.0056(1.8) I-014: ¹H-NMR(400.0 MHz,CDCl3): δ = 8.6990(2.4); 8.6971(2.5); 8.2861(2.5); 8.2831(2.5);7.2634(4.8); 4.4174(1.6); 4.4028(3.2); 4.3875(1.8); 4.0394(16.0);3.6277(14.8); 3.0557(1.6); 3.0396(3.2); 3.0238(1.6); 2.1429(0.4);2.1285(0.9); 2.1145(1.6); 2.1025(1.4); 2.0902(0.6); 2.0851(0.7);2.0478(0.7); 2.0323(1.5); 2.0175(1.5); 2.0047(1.0); 1.9893(0.4);0.0077(0.7); −0.0002(16.1) I-015: ¹H-NMR(400.0 MHz, CDCl3): δ =8.0694(1.0); 7.5754(2.0); 7.5546(3.3); 7.4953(0.7); 7.2645(10.7);4.3949(2.3); 4.3812(4.3); 4.3665(2.6); 3.9140(16.0); 3.8059(1.1);3.7877(3.2); 3.7694(3.2); 3.7517(1.2); 3.0372(2.6); 2.9985(1.4);2.9821(1.4); 2.9800(1.5); 2.9609(0.5); 2.1015(2.7); 2.0904(2.6);2.0236(2.5); 2.0132(2.6); 1.7553(0.5); 1.7502(0.5); 1.4242(5.0);1.4060(10.6); 1.3877(5.2); 1.2541(0.9); 0.0707(0.5); −0.0002(20.0)I-016: ¹H-NMR(400.0 MHz, CDCl3): δ = 8.1141(1.0); 8.0587(0.4);7.5888(3.0); 7.5687(5.2); 7.5227(1.0); 7.2639(58.1); 6.9998(0.4);5.3007(2.6); 4.3958(4.5); 3.9456(16.0); 3.6088(10.6); 3.0407(3.6);2.1717(0.4); 2.1176(3.7); 2.0297(3.6); 1.9423(0.3); 1.8818(0.4);1.6886(7.9); 1.5068(0.3); 1.2528(0.7); 0.1459(0.8); 0.0074(6.8);−0.0002(160.2); −0.1498(0.8) I-017: ¹H-NMR(400.0 MHz, CDCl3): δ =8.6438(4.3); 8.2741(1.3); 7.2662(13.5); 5.3011(0.6); 4.3978(3.2);4.3832(1.9); 4.0270(16.0); 3.8541(0.9); 3.8361(2.5); 3.8180(2.6);3.8005(1.0); 3.5096(0.5); 3.0436(2.3); 3.0205(1.5); 3.0015(2.7);2.9880(5.8); 2.9831(3.2); 2.9639(0.9); 2.8958(0.4); 2.6271(4.4);2.1120(2.1); 2.1018(2.1); 2.0280(2.0); 1.7509(1.7); 1.6460(0.4);1.6224(0.4); 1.5807(0.7); 1.5639(0.7); 1.4781(0.3); 1.4469(3.4);1.4286(9.2); 1.4096(8.1); 1.3907(2.9); 1.3335(1.1); 1.2991(0.9);1.2847(1.8); 1.2778(1.4); 1.2558(9.4); 1.2326(0.8); 1.2153(0.6);1.1980(0.5); 1.0241(0.3); 1.0072(0.4); 0.8962(1.0); 0.8798(1.8);0.8592(2.3); 0.8528(2.2); 0.8430(2.7); 0.8307(2.2); 0.8108(1.6);0.7948(1.0); 0.0708(1.0); 0.0078(1.4); −0.0002(34.5) I-018: ¹H-NMR(400.0MHz, CDCl3): δ = 8.6497(3.3); 8.2749(1.3); 7.2647(16.4); 5.3011(0.4);4.4208(1.4); 4.4073(2.5); 4.3927(1.4); 4.0467(12.9); 3.6406(8.2);3.5127(0.8); 3.0570(1.3); 3.0443(2.2); 2.9879(2.2); 2.6240(16.0);2.1223(1.6); 2.1134(1.5); 2.0357(1.5); 2.0258(1.5); 1.7154(2.9);1.2546(0.5); 0.0077(2.2); −0.0002(48.4); −0.0083(2.2) I-019:¹H-NMR(499.9 MHz, d₆-DMSO): δ = 8.1711(0.3); 8.0131(5.9); 4.2911(1.9);4.2796(3.7); 4.2677(2.0); 4.0281(16.0); 3.9503(0.9); 3.9412(0.5);3.9277(1.1); 3.9144(1.5); 3.9010(1.1); 3.8875(0.5); 3.6548(1.2);3.6401(3.8); 3.6253(3.8); 3.6105(1.2); 3.3287(30.1); 2.9565(1.8);2.9439(3.8); 2.9314(2.1); 2.6368(0.5); 2.5048(71.1); 2.5019(88.8);2.3629(0.6); 2.0751(1.6); 2.0250(2.1); 2.0159(1.9); 1.9300(2.0);1.9184(2.1); 1.9083(1.5); 1.3742(15.9); 1.3609(16.0); 1.3168(1.0);1.3034(1.0); 1.2551(4.2); 1.2404(9.1); 1.2256(4.3); 1.2046(0.4);1.1469(0.3); −0.0002(7.9) I-020: ¹H-NMR(400.0 MHz, CDCl3): δ =8.6407(3.5); 8.6365(3.5); 8.3480(3.0); 8.3443(2.9); 7.2635(9.5);5.3000(1.9); 4.4058(1.6); 4.3919(3.0); 4.3767(1.8); 4.0073(16.0);3.8607(0.8); 3.8424(2.2); 3.8242(2.2); 3.8057(0.8); 3.0544(1.7);3.0383(3.2); 3.0230(1.6); 2.1071(1.7); 2.0960(1.6); 2.0451(1.2);2.0305(1.6); 2.0172(1.6); 1.4451(2.6); 1.4272(5.8); 1.4092(2.5);1.2591(0.4); −0.0002(23.7); −0.0084(0.9) I-021: ¹H-NMR(400.0 MHz,CDCl3): δ = 9.0106(5.6); 9.0063(6.1); 8.6408(5.1); 8.6369(5.4);7.2622(51.7); 5.3006(3.7); 4.4097(3.7); 4.0798(16.0); 3.8451(2.4);3.8293(2.4); 3.0618(3.4); 2.1229(2.7); 2.0405(2.6); 1.8292(2.9);1.4522(6.7); 1.2541(1.0); 0.1458(0.5); 0.1263(0.4); 0.0077(3.8);−0.0003(104.8); −0.1496(0.5) I-022: ¹H-NMR(400.0 MHz, CDCl3): δ =8.7294(3.5); 8.5218(3.4); 7.2626(14.6); 5.3004(2.1); 4.4635(0.5);4.4146(1.7); 4.4007(3.3); 4.3858(1.9); 4.0503(16.0); 3.8679(0.9);3.8492(2.3); 3.8310(2.4); 3.8123(0.9); 3.0646(1.8); 3.0487(3.4);3.0344(1.7); 2.1161(1.9); 2.1053(1.9); 2.0379(1.9); 2.0258(1.9);1.8284(0.4); 1.7920(0.4); 1.7843(0.4); 1.4579(2.9); 1.4398(6.2);1.4218(2.9); 1.2561(0.7); 0.0692(0.8); −0.0002(30.9) I-023: ¹H-NMR(400.0MHz, CDCl3): δ = 8.6419(4.9); 8.3521(2.7); 7.2614(33.3); 5.3001(2.0);4.4035(4.3); 4.3896(2.6); 4.0246(16.0); 4.0004(0.6); 3.6315(11.5);3.0398(3.9); 2.9868(2.4); 2.1185(2.9); 2.1088(2.8); 2.0311(2.8);2.0203(2.9); 1.6151(0.7); 1.2549(0.8); −0.0002(52.4) I-024: ¹H-NMR(499.9MHz, d₆-DMSO): δ = 9.2130(4.2); 8.2367(4.5); 4.8376(1.0); 4.8279(2.0);4.8186(1.0); 4.4234(0.4); 4.4135(0.8); 4.4027(0.5); 4.3971(0.6);4.3868(1.1); 4.3766(0.5); 4.2197(0.5); 4.2104(0.6); 4.2026(0.6);4.1929(0.9); 4.1837(0.5); 4.1759(0.5); 4.1661(0.4); 4.0536(0.8);4.0393(2.4); 4.0251(2.5); 4.0099(16.0); 3.7825(1.0); 3.7677(3.4);3.7529(3.5); 3.7382(1.1); 2.5101(4.8); 2.5066(6.3); 2.5031(4.6);2.2223(0.4); 2.2174(0.5); 2.2129(0.4); 2.2059(0.5); 2.2002(0.5);2.1967(0.5); 2.1867(0.4); 2.0931(0.4); 2.0880(0.4); 2.0842(0.4);2.0709(0.7); 2.0678(0.7); 2.0626(0.7); 2.0501(0.4); 2.0456(0.4);2.0372(0.3); 1.9924(10.3); 1.9655(0.5); 1.9498(0.6); 1.9461(0.6);1.9351(0.6); 1.9245(0.6); 1.9204(0.6); 1.9154(0.4); 1.9097(0.5);1.2920(3.8); 1.2772(8.1); 1.2624(3.7); 1.1907(2.6); 1.1765(5.2);1.1623(2.6) I-025: ¹H-NMR(601.6 MHz, CD3CN): δ = 8.2955(5.5);7.2535(2.0); 7.1637(4.4); 7.0739(2.1); 4.3307(2.8); 4.3206(4.9);4.3105(2.9); 4.2870(0.4); 4.2765(0.3); 4.2726(0.3); 4.0593(6.6);4.0564(13.3); 4.0534(7.1); 3.8139(0.6); 3.7920(0.6); 3.7639(0.6);3.7612(0.5); 3.5785(2.2); 3.5661(7.2); 3.5538(7.3); 3.5415(2.3);2.9888(2.6); 2.9780(5.4); 2.9673(2.8); 2.9418(0.4); 2.9324(0.4);2.5328(7.7); 2.1807(86.1); 2.1128(1.0); 2.1074(0.9); 2.1034(1.8);2.0976(1.7); 2.0931(2.9); 2.0871(2.0); 2.0830(2.6); 2.0786(1.4);2.0734(1.4); 2.0616(0.4); 2.0570(0.5); 2.0513(0.4); 2.0477(0.5);2.0152(1.0); 2.0114(0.6); 2.0046(2.5); 2.0007(1.6); 1.9924(25.5);1.9843(11.5); 1.9802(11.6); 1.9763(46.4); 1.9722(76.3); 1.9681(111.5);1.9640(75.2); 1.9599(37.7); 1.9512(1.6); 1.9432(0.8); 1.9392(0.6);1.8575(0.5); 1.8534(0.7); 1.8493(0.5); 1.3441(7.5); 1.3319(16.0);1.3238(0.6); 1.3195(7.6); 1.3116(0.7); 1.3015(0.5); 1.2990(0.5);1.2859(0.7); 1.2823(0.5); 1.2800(0.4); 1.2735(0.4); 1.2698(0.8);1.2677(0.6); 1.2574(0.4) I-026: ¹H-NMR(601.6 MHz, CD3CN): δ =9.0587(1.3); 8.1305(1.4); 8.1291(1.4); 5.7906(0.4); 5.7062(0.4);4.0221(9.6); 4.0117(0.6); 3.7546(0.6); 3.7423(1.9); 3.7299(1.9);3.7176(0.6); 2.5315(16.0); 2.1943(0.6); 2.1680(40.6); 2.0787(0.4);1.9924(13.1); 1.9843(5.4); 1.9802(5.9); 1.9763(25.0); 1.9722(42.4);1.9681(61.6); 1.9640(40.9); 1.9599(20.8); 1.8533(0.4); 1.3737(2.1);1.3614(4.5); 1.3558(0.4); 1.3491(2.1) I-027: The NMR spectroscopy datafor Example I-027 can be found in the above section relating to thepreparation examples. I-028: ¹H-NMR(601.6 MHz, CDCl3): δ = 8.3760(1.5);8.3726(1.5); 7.9247(1.1); 7.2623(5.2); 5.2976(4.9); 4.3974(1.4);4.3874(2.5); 4.3772(1.4); 3.9896(16.0); 3.8315(0.9); 3.8191(2.9);3.8068(3.0); 3.7944(0.9); 3.0461(1.2); 3.0353(2.3); 3.0246(1.2);2.1087(0.7); 2.1030(0.8); 2.0987(1.2); 2.0924(0.9); 2.0891(1.0);2.0829(0.4); 2.0791(0.5); 2.0335(0.4); 2.0303(0.3); 2.0231(1.1);2.0197(0.8); 2.0130(1.1); 2.0039(0.8); 1.4289(3.2); 1.4166(6.9);1.4042(3.2); −0.0002(3.7) I-029: ¹H-NMR(601.6 MHz, CDCl3): δ =8.8369(3.9); 7.7068(3.1); 7.2632(14.4); 5.2979(7.5); 4.3905(2.0);4.3806(3.7); 4.3705(2.1); 4.0244(0.4); 3.9895(16.0); 3.7904(0.4);3.7823(1.1); 3.7701(3.3); 3.7571(6.1); 3.7451(1.5); 3.7390(3.7);3.7212(1.3); 3.0452(1.8); 3.0345(3.6); 3.0240(2.0); 2.6184(6.1);2.1200(0.7); 2.1101(1.5); 2.1006(2.4); 2.0913(2.1); 2.0811(1.0);2.0339(0.9); 2.0235(2.2); 2.0135(2.2); 2.0045(1.6); 1.9940(0.6);1.4172(5.2); 1.4048(11.0); 1.3925(5.2); 1.2561(0.9); 0.0052(0.5);−0.0002(15.4); −0.0057(0.5) I-030: The NMR spectroscopy data for ExampleI-030 can be found in the above section relating to the preparationexamples. I-031: ¹H-NMR(400.0 MHz, CDCl3): δ = 8.9089(2.2); 8.0784(1.9);7.2647(4.4); 5.3008(3.5); 4.4072(1.0); 4.3913(1.8); 4.3754(1.0);4.0443(10.2); 3.8167(0.6); 3.7982(1.8); 3.7796(1.9); 3.7611(0.6);2.8083(3.9); 1.9122(1.0); 1.8961(1.8); 1.8803(1.0); 1.6315(2.2);1.4304(2.3); 1.4119(5.0); 1.3933(2.2); 1.1530(16.0); −0.0002(1.9) I-032:¹H-NMR(400.0 MHz, CDCl3): δ = 8.8689(4.4); 8.0886(4.6); 7.6016(0.7);7.5845(0.7); 7.4450(2.9); 7.4240(2.6); 7.3397(2.3); 7.2624(12.4);6.9798(0.7); 6.8519(0.4); 6.8181(0.4); 5.3001(1.7); 4.2986(16.0);4.1101(2.6); 4.0965(4.1); 4.0815(2.2); 3.9296(1.2); 3.9047(3.4);3.8797(3.4); 3.8547(1.2); 2.9864(2.4); 2.9707(4.3); 2.9555(2.0);2.0826(2.4); 2.0716(2.3); 2.0175(2.4); 2.0033(2.2); 1.6935(6.0);−0.0004(7.1) I-033: ¹H-NMR(400.0 MHz, CDCl3): δ = 8.0508(2.2);7.5783(0.9); 7.5754(0.9); 7.5570(1.4); 7.5542(1.4); 7.4798(1.9);7.4585(1.2); 7.2615(12.7); 4.6519(0.4); 4.6445(0.5); 4.6379(0.5);4.6304(0.4); 4.6167(0.4); 4.6098(0.6); 4.6034(0.6); 4.5956(0.5);4.1909(0.3); 4.1788(0.4); 4.1618(0.4); 4.1485(0.6); 4.1279(0.4);4.1157(0.3); 3.9139(16.0); 3.8501(0.4); 3.8320(0.6); 3.8149(1.4);3.8032(0.5); 3.7963(1.3); 3.7848(1.3); 3.7777(0.5); 3.7663(1.4);3.7489(0.6); 3.7311(0.4); 3.1909(0.5); 3.1866(0.5); 3.1747(0.5);3.1476(0.6); 3.1441(0.6); 3.1356(0.6); 3.1316(0.6); 2.5961(0.6);2.5706(0.7); 2.5537(0.6); 2.5273(0.7); 2.1726(0.5); 2.1653(0.6);2.1605(0.6); 2.1359(1.0); 2.0067(0.4); 1.7656(0.4); 1.7586(0.3);1.7518(0.5); 1.7378(0.3); 1.7306(0.4); 1.7235(0.3); 1.7164(0.4);1.6066(1.0); 1.4214(3.4); 1.4028(7.3); 1.3842(3.3); 1.2100(5.2);1.1938(5.1); 0.0079(0.4); −0.0002(10.3); −0.0085(0.4) I-034:¹H-NMR(400.0 MHz, CDCl3): δ = 8.9298(3.1); 8.1001(3.3); 7.2631(7.0);5.3003(2.2); 4.6622(0.4); 4.6553(0.5); 4.6490(0.5); 4.6413(0.4);4.6273(0.4); 4.6209(0.5); 4.6142(0.6); 4.6064(0.5); 4.1903(0.4);4.1736(0.4); 4.1618(0.5); 4.1387(0.4); 4.1271(0.3); 4.0440(16.0);3.8527(0.4); 3.8345(0.6); 3.8174(1.4); 3.8056(0.5); 3.7988(1.4);3.7872(1.4); 3.7805(0.5); 3.7687(1.4); 3.7515(0.7); 3.7335(0.4);3.2034(0.5); 3.1920(0.5); 3.1874(0.5); 3.1605(0.6); 3.1571(0.6);3.1481(0.6); 3.1444(0.6); 2.6071(0.6); 2.5812(0.7); 2.5637(0.6);2.5378(0.7); 2.1797(0.6); 2.1755(0.5); 2.1678(0.4); 2.1552(0.8);2.1461(0.9); 1.7760(0.4); 1.7622(0.5); 1.7407(0.4); 1.7268(0.4);1.5983(1.9); 1.4364(3.4); 1.4178(7.4); 1.3992(3.4); 1.2190(5.2);1.2027(5.1); 0.0703(0.9); −0.0002(5.2) I-035: ¹H-NMR(400.0 MHz, CDCl3):δ = 8.6380(2.2); 8.6340(2.1); 8.2446(2.3); 8.2406(2.1); 7.2630(7.4);4.6675(0.4); 4.6607(0.5); 4.6543(0.5); 4.6472(0.4); 4.6329(0.5);4.6261(0.6); 4.6197(0.6); 4.6120(0.5); 4.2042(0.4); 4.1934(0.4);4.1764(0.5); 4.1671(0.6); 4.1418(0.4); 4.1298(0.4); 4.0237(16.0);3.8958(0.4); 3.8777(0.7); 3.8606(1.4); 3.8422(1.5); 3.8259(1.5);3.8075(1.4); 3.7903(0.7); 3.7723(0.5); 3.2047(0.5); 3.1921(0.5);3.1880(0.5); 3.1614(0.6); 3.1579(0.6); 3.1481(0.6); 2.6063(0.7);2.5802(0.8); 2.5633(0.6); 2.5374(0.7); 2.1820(0.6); 2.1748(0.7);2.1443(1.1); 2.0074(0.4); 1.7733(0.5); 1.7662(0.4); 1.7595(0.5);1.7525(0.4); 1.7449(0.4); 1.7385(0.5); 1.7316(0.4); 1.7245(0.4);1.6214(1.8); 1.4411(3.4); 1.4225(7.2); 1.4039(3.3); 1.2546(0.4);1.2165(5.3); 1.2003(5.3); 0.0700(0.9); −0.0002(4.1) I-036: ¹H-NMR(400.0MHz, CDCl3): δ = 8.3755(2.0); 8.3700(2.0); 8.0353(0.3); 7.9187(1.8);7.9163(1.8); 7.2641(5.5); 4.6598(0.4); 4.6532(0.6); 4.6465(0.6);4.6388(0.5); 4.6247(0.5); 4.6182(0.6); 4.6116(0.6); 4.6039(0.5);4.1979(0.3); 4.1859(0.4); 4.1697(0.5); 4.1591(0.6); 4.1351(0.5);4.1231(0.4); 3.9893(16.0); 3.8784(0.4); 3.8606(0.7); 3.8433(1.4);3.8249(1.4); 3.8092(1.6); 3.7909(1.5); 3.7739(0.9); 3.7663(0.4);3.7558(0.5); 3.1971(0.5); 3.1811(0.6); 3.1540(0.6); 3.1508(0.6);3.1419(0.6); 3.1386(0.6); 3.0233(1.8); 2.5999(0.7); 2.5738(0.8);2.5565(0.6); 2.5308(0.8); 2.1756(0.6); 2.1689(0.7); 2.1389(1.1);2.1279(0.8); 1.7686(0.5); 1.7617(0.4); 1.7544(0.6); 1.7479(0.4);1.7403(0.4); 1.7333(0.6); 1.7263(0.5); 1.7198(0.6); 1.7031(0.6);1.6903(0.6); 1.4310(3.4); 1.4125(7.2); 1.3939(3.4); 1.3623(0.6);1.3438(1.3); 1.3252(0.6); 1.2119(5.4); 1.1957(5.4); 1.1834(1.1);1.1669(1.0); 0.0702(1.5); −0.0002(2.7) I-037: ¹H-NMR(601.6 MHz, CDCl3):δ = 8.9272(3.0); 8.0880(3.1); 8.0871(3.1); 7.2599(8.9); 5.2978(0.5);5.0935(0.8); 5.0782(2.4); 5.0628(2.5); 5.0475(0.8); 4.4037(1.4);4.3938(2.5); 4.3836(1.4); 4.1583(16.0); 3.0645(1.4); 3.0536(2.8);3.0430(1.4); 2.1194(0.3); 2.1098(0.8); 2.1041(0.8); 2.0999(1.3);2.0935(0.9); 2.0902(1.0); 2.0841(0.4); 2.0802(0.5); 2.0380(0.5);2.0348(0.4); 2.0275(1.3); 2.0242(0.8); 2.0172(1.2); 2.0082(0.8);1.5550(7.2); 1.2555(0.5); 0.0052(0.4); −0.0002(10.7); −0.0057(0.4)I-038: ¹H-NMR(601.6 MHz, CDCl3): δ = 8.8882(2.6); 7.9976(2.8);7.9963(2.9); 7.2597(21.8); 5.2982(0.4); 4.7308(0.5); 4.7193(0.4);4.7070(0.5); 4.6972(0.4); 4.3758(0.6); 4.3591(0.8); 4.3524(1.1);4.3484(16.0); 4.3430(0.7); 4.3358(1.1); 4.3231(0.5); 4.3196(0.6);4.3115(0.5); 4.3008(0.3); 4.2173(0.3); 4.1638(0.8); 4.1588(1.4);4.1477(0.8); 4.1406(0.6); 4.1244(0.6); 4.0140(0.5); 3.0476(1.3);3.0368(2.3); 3.0261(1.1); 2.1105(0.5); 2.0998(0.8); 2.0900(0.8);2.0786(0.5); 2.0446(0.4); 2.0341(0.9); 2.0268(0.8); 2.0236(1.1);2.0202(0.7); 2.0159(0.6); 2.0129(0.7); 2.0089(0.4); 1.5478(12.4);1.2552(1.6); 0.8803(0.4); 0.0052(0.9); −0.0002(26.2); −0.0057(0.8)I-039: ¹H-NMR(499.9 MHz, d₆-DMSO): δ = 8.0232(5.4); 4.3032(1.8);4.2915(3.2); 4.2795(1.7); 4.0713(16.0); 3.6947(1.2); 3.6800(3.7);3.6652(3.7); 3.6505(1.2); 3.4077(0.4); 3.3868(0.4); 3.3800(0.4);3.1818(1.9); 3.0250(0.4); 3.0060(15.3); 2.9631(1.8); 2.9503(3.5);2.9377(1.8); 2.5154(0.4); 2.5121(0.8); 2.5085(1.0); 2.5050(0.8);2.0818(1.3); 2.0514(0.5); 2.0395(1.2); 2.0289(1.8); 2.0203(1.6);2.0060(0.7); 1.9459(0.7); 1.9424(0.7); 1.9339(1.7); 1.9221(1.7);1.9114(1.2); 1.8993(0.5); 1.2787(4.1); 1.2640(8.8); 1.2492(4.0) I-040:¹H-NMR(499.9 MHz, d₆-DMSO): δ = 8.0277(5.0); 4.2985(1.6); 4.2868(2.6);4.2746(1.3); 4.0815(0.4); 4.0742(0.6); 4.0700(1.0); 4.0446(16.0);3.6723(1.2); 3.6575(3.6); 3.6427(3.5); 3.6280(1.1); 3.3853(2.3);3.3704(5.1); 3.3554(6.1); 3.3400(5.6); 3.3244(246.1); 3.0090(0.6);2.9626(1.4); 2.9498(2.8); 2.9371(1.4); 2.5154(7.4); 2.5118(14.2);2.5082(18.9); 2.5045(13.2); 2.5009(5.9); 2.0542(0.5); 2.0426(1.0);2.0358(1.2); 2.0311(1.4); 2.0225(1.2); 2.0078(0.5); 1.9490(0.6);1.9453(0.6); 1.9369(1.4); 1.9329(1.2); 1.9250(1.3); 1.9140(0.9);1.4965(0.4); 1.3797(4.7); 1.3648(9.8); 1.3498(4.5); 1.2892(0.4);1.2741(0.7); 1.2672(4.0); 1.2524(8.7); 1.2376(3.8) I-041: ¹H-NMR(400.0MHz, CDCl3): δ = 8.6907(2.3); 8.2739(2.4); 8.2703(2.4); 7.2653(5.2);4.6626(0.4); 4.6563(0.5); 4.6495(0.6); 4.6417(0.5); 4.6277(0.5);4.6213(0.6); 4.6144(0.6); 4.6070(0.5); 4.2021(0.4); 4.1901(0.5);4.1738(0.5); 4.1627(0.6); 4.1394(0.4); 4.1273(0.4); 4.0143(16.0);3.8738(0.4); 3.8557(0.8); 3.8385(1.4); 3.8257(0.5); 3.8201(1.4);3.8074(1.4); 3.7890(1.5); 3.7711(0.8); 3.7538(0.4); 3.2029(0.6);3.1875(0.6); 3.1572(0.7); 3.1443(0.7); 2.6058(0.7); 2.5797(0.9);2.5623(0.7); 2.5366(0.8); 2.1807(0.6); 2.1739(0.7); 2.1439(1.1);2.0074(1.3); 1.7724(0.5); 1.7651(0.4); 1.7586(0.6); 1.7520(0.4);1.7442(0.4); 1.7375(0.5); 1.7298(0.4); 1.7233(0.5); 1.6547(2.1);1.4368(3.6); 1.4183(7.4); 1.3997(3.5); 1.2156(5.7); 1.1995(5.6);−0.0002(2.2) I-042: ¹H-NMR(601.6 MHz, CDCl3): δ = 8.6309(2.0);8.6277(2.1); 8.3288(1.9); 8.3256(1.9); 7.2597(46.7); 5.2983(0.4);4.6500(0.4); 4.6456(0.4); 4.6404(0.4); 4.6313(0.4); 4.6268(0.4);4.6225(0.4); 4.6173(0.4); 4.1706(0.3); 4.1626(0.4); 4.0007(16.0);3.8705(0.5); 3.8582(0.7); 3.8471(1.2); 3.8348(1.1); 3.8221(0.4);3.8085(1.1); 3.7962(1.2); 3.7850(0.7); 3.7728(0.5); 3.1877(0.4);3.1850(0.4); 3.1796(0.4); 3.1766(0.4); 3.1590(0.4); 3.1562(0.4);3.1507(0.4); 3.1481(0.4); 2.5895(0.5); 2.5721(0.5); 2.5607(0.5);2.5434(0.5); 2.1704(0.4); 2.1656(0.5); 2.1622(0.4); 2.1573(0.3);2.1466(0.6); 2.1411(0.6); 1.7627(0.3); 1.7535(0.4); 1.7396(0.3);1.5455(96.7); 1.4287(3.2); 1.4163(7.0); 1.4040(3.1); 1.2108(4.4);1.2000(4.5); 0.0052(2.0); −0.0002(71.9); −0.0057(2.2) I-043: The NMRspectroscopy data for Example I-043 can be found in the above sectionrelating to the preparation examples. I-044: The NMR spectroscopy datafor Example I-044 can be found in the above section relating to thepreparation examples. I-045: The NMR spectroscopy data for Example I-045can be found in the above section relating to the preparation examples.

Use Examples

Ctenocephalides felis—In Vitro Contact Tests with Adult Cat Fleas

For the coating of the test tubes, 9 mg of active ingredient are firstdissolved in 1 ml of acetone p.a. and then diluted to the desiredconcentration with acetone p.a. 250 μl of the solution are distributedhomogeneously on the inner walls and the base of a 25 ml glass tube byturning and rocking on an orbital shaker (rocking rotation at 30 rpm for2 h). With 900 ppm of active ingredient solution and internal surfacearea 44.7 cm², given homogeneous distribution, an area-based dose of 5μg/cm² is achieved.

After the solvent has evaporated off, the tubes are populated with 5-10adult cat fleas (Ctenocephalides felis), sealed with a perforatedplastic lid and incubated in a horizontal position at room temperatureand ambient humidity. After 48 h, efficacy is determined. To this end,the tubes are stood upright and the fleas are knocked to the base of thetube. Fleas which remain motionless at the base or move in anuncoordinated manner are considered to be dead or moribund.

A substance shows good efficacy against Ctenocephalides felis if atleast 80% efficacy was achieved in this test at an application rate of 5μg/cm². 100% efficacy means that all the fleas were dead or moribund. 0%efficacy means that no fleas were harmed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 5 μg/cm²(=500 g/ha): I-001, I-007

Boophilus microplus—Injection Test

Solvent: dimethyl sulfoxide

To produce a suitable active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of solvent and the concentrate isdiluted to the desired concentration with solvent.

1 μl of the active ingredient solution is injected into the abdomen of 5engorged adult female cattle ticks (Boophilus microplus). The animalsare transferred into dishes and kept in a climate-controlled room.

Efficacy is assessed after 7 days by laying of fertile eggs. Eggs whichare not visibly fertile are stored in a climate-controlled cabinet untilthe larvae hatch after about 42 days. An efficacy of 100% means thatnone of the ticks has laid any fertile eggs; 0% means that all the eggsare fertile.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20μg/animal: I-009

Ctenocephalides felis—Oral Test

Solvent: dimethyl sulfoxide

To produce a suitable active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulfoxide. Dilution withcitrated cattle blood gives the desired concentration.

About 20 unfed adult cat fleas (Cienocephalides felis) are placed into achamber which is closed at the top and bottom with gauze. A metalcylinder whose bottom end is closed with parafilm is placed onto thechamber. The cylinder contains the blood/active ingredient formulation,which can be imbibed by the fleas through the parafilm membrane.

After 2 days, the kill in % is determined. 100% means that all of thefleas have been killed; 0% means that none of the fleas have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm:I-012

In this test, for example, the following compounds from the preparationexamples show an efficacy of 95% at an application rate of 100 ppm:I-011, I-013

In this test, for example, the following compounds from the preparationexamples show an efficacy of 80% at an application rate of 100 ppm:I-007, I-009

Lucilia cuprina Test

Solvent: dimethyl sulfoxide

To produce a suitable active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulfoxide, and theconcentrate is diluted with water to the desired concentration.

About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) aretransferred into a test vessel containing minced horsemeat and theactive ingredient formulation of the desired concentration.

After 2 days, the kill in % is determined. 100% means that all thelarvae have been killed; 0% means that no larvae have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm:I-007, I-009, I-011, I-012, I-013, I-014, I-015

Musca domestica Test

Solvent: dimethyl sulfoxide

To produce a suitable active ingredient formulation, 10 mg of activeingredient are mixed with 0.5 ml of dimethyl sulfoxide, and theconcentrate is diluted with water to the desired concentration.

Vessels containing a sponge treated with sugar solution and the activeingredient formulation of the desired concentration are populated with10 adult houseflies (Musca domestica).

After 2 days, the kill in % is determined. 100% means that all of theflies have been killed; 0% means that none of the flies have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm:I-007, I-009-I-014

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 ppm:I-015

In this test, for example, the following compounds from the preparationexamples show an efficacy of 80% at an application rate of 100 ppm:I-011, I-013

Meloidogyne incognita Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is mixed with the stated amount of solvent and theconcentrate is diluted to the desired concentration with water.

Vessels are filled with sand, active ingredient solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.The galls develop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compound from the preparationexamples shows an efficacy of 90% at an application rate of 20 ppm:I-012

Myzus persicae—Oral Test

Solvent: 100 parts by weight of acetone

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the stated parts by weight ofsolvent and made up to the desired concentration with water.

50 μl of the active ingredient preparation are transferred intomicrotitre plates and made up to a final volume of 200 μl with 150 μl ofIPL41 insect medium (33%+15% sugar). Subsequently, the plates are sealedwith parafilm, which a mixed population of green peach aphids (Myzuspersicae) within a second microtitre plate is able to puncture andimbibe the solution.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 4 ppm:I-003, I-004, I-006, I-007, I-009, I-010, I-011, I-012, I-013, I-014,I-015, I-016, I-017, I-018, I-019, I-020, I-021, I-022, I-023, I-024,I-025

Myzus persicae—Spray Test

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive ingredient formulation of the desired concentration.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha:I-002

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-003, I-007, I-009, I-017, I-021

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 g/ha:I-002, I-011, I-012, I-013, I-014, I-015, I-019, I-020, I-023, I-024

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 g/ha:I-007

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 20 g/ha:I-002, I-009, I-010, I-011, I-012, I-015, I-017, I-018, I-019, I-020,1-021, I-022, I-023

Phaedon cochleariae—Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active ingredient formulation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined. 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 500 g/ha:I-002

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-012, I-020, I-021

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 100 g/ha:I-013, I-015

Spodoptera frugiperda—Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Leaf discs of maize (Zea mays) are sprayed with an active ingredientformulation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined. 100% means that all thecaterpillars have been killed; 0% means that no caterpillar has beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 g/ha:I-017

In this test, for example, the following compounds from the preparationexamples show an efficacy of 83% at an application rate of 100 g/ha:I-010, 1-012

Tetranychus urticae—Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive ingredient formulation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that no spider mites have beenkilled.

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 90% at an application rate of 100 g/ha:I-003

1. A compound of formula (I)

wherein Aa is —N(R⁷)—, —S(O)m-, —O—, —C(R⁸)(R⁹)— or carbonyl, Ab is—N(R⁷)—, —S(O)m-, —O—, —C(R¹⁰)(R¹¹)— or carbonyl, Ac is —N(R⁷)—,—S(O)m-, —O—, —C(R¹²)(R¹³)— or carbonyl, Ad is —N(R⁷)—, —S(O)m-, —O—,—C(R¹⁴)(R¹⁵)— or carbonyl, where not more than two of the Aa, Ab, Ac andAd substituents at the same time can be —N(R⁷)—, —O— or —S(O)m-, R¹ is(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, amino, (C₁-C₆)-alkylamino,di-(C₁-C₆)-alkyl-amino, (C₃-C₈)-cycloalkylamino,(C₁-C₆)-alkylcarbonylamino, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonylamino,aminosulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl,di-(C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl, or is in each caseoptionally identically or differently mono- or poly-aryl-, -hetaryl- or-heterocyclyl-substituted (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, where aryl,hetaryl or heterocyclyl may each optionally be mono- or polysubstitutedidentically or differently by halogen, cyano, nitro, hydroxyl, amino,carboxyl, carbamoyl, aminosulfonyl, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy,(C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkylsulfimino, (C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkylsulfoximino,(C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-alkylcarbonyl, (C₃-C₆)-trialkylsilyl or benzyl, or R¹ is aryl,hetaryl or heterocyclyl, each of which is optionally mono- orpolysubstituted identically or differently by halogen, cyano, nitro,hydroxyl, amino, carboxyl, carbamoyl, (C₁-C₆)-alkyl, (C₃-C₈)-cycloalkyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy,(C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkylsulfimino, (C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkylsulfoximino,(C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-alkylcarbonyl, (C₃-C₆)-trialkylsilyl, (═O) (in the case ofheterocyclyl only) and (═O)₂ (in the case of heterocyclyl only), R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are independently hydrogen, cyano, halogen,nitro, acetyl, hydroxyl, amino, SCN, tri-(C₁-C₆)-alkylsilyl,(C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,(C₁-C₆)-alkylhydroxyimino, (C₁-C₆)-alkoxyimino,(C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,(C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,(C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,(C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,(C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,(C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,(C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,(C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,(C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl((C₁-C₆)-alkylcarbonylamino), are in each case optionally singly ormultiply, identically or differently substituted aryl or hetaryl, where(in the case of hetaryl) at least one carbonyl group may optionally bepresent and/or where possible substituents in each case are as follows:cyano, carboxyl, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri-(C₁-C₆)alkylsilyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,(C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl,(C₂-C₆)haloalkynyl, (C₂-C₆)cyanoalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)cyanoalkoxy,(C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkoxy,(C₁-C₆)alkylhydroxyimino, (C₁-C₆)alkoxyimino,(C₁-C₆)alkyl-(C₁-C₆)alkoxyimino, (C₁-C₆)haloalkyl-(C₁-C₆)alkoxyimino,(C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkoxy-(C₁-C₆)alkylthio,(C₁-C₆)alkylthio-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfinyl,(C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, (C₁-C₆)alkoxy-(C₁-C₆)alkylsulfonyl,(C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyloxy,(C₁-C₆)alkylcarbonyl, (C₁-C₆)haloalkylcarbonyl, (C₁-C₆)alkylcarbonyloxy,(C₁-C₆)alkoxycarbonyl, (C₁-C₆)haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)alkylaminocarbonyl, di-(C₁-C₆)alkylaminocarbonyl,(C₂-C₆)alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)cycloalkylaminocarbonyl, (C₁-C₆)alkylsulfonylamino,(C₁-C₆)alkylamino, di-(C₁-C₆)alkylamino, aminosulfonyl,(C₁-C₆)alkylaminosulfonyl, di-(C₁-C₆)alkylaminosulfonyl,(C₁-C₆)alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)alkylaminothiocarbonyl, di-(C₁-C₆)alkylaminothiocarbonyl,(C₃-C₈)cycloalkylamino, (C₁-C₆)alkylcarbonylamino, R⁷ is hydrogen,(C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₁-C₆)cyanoalkyl, (C₁-C₆)hydroxyalkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkenyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkenyloxy-(C₁-C₆)alkyl, (C₂-C₆)haloalkenyl,(C₂-C₆)cyanoalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₂-C₆)haloalkynyl, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkyl-(C₃-C₈)cycloalkyl, (C₁-C₆)alkyl-(C₃-C₈)cycloalkyl,halo(C₃-C₈)cycloalkyl, (C₁-C₆)alkylthio-(C₁-C₆)alkyl,(C₁-C₆)alkylsulfinyl-(C₁-C₆)alkyl, (C₁-C₆)alkylsulfonyl-(C₁-C₆)alkyl or(C₁-C₆)alkylcarbonyl-(C₁-C₆)alkyl, Q is a partly saturated or saturatedheterocyclic or heteroaromatic 8-, 9-, 10-, 11- or 12-membered fusedbicyclic or tricyclic ring system where at least one carbonyl group mayoptionally be present and/or where the ring system is optionally mono-or polysubstituted identically or differently, and where thesubstituents may independently be selected from cyano, halogen, nitro,acetyl, hydroxyl, amino, SCN, tri-(C₁-C₆)-alkylsilyl,(C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₆)-haloalkynyl,(C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,(C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₁-C₆)-cyanoalkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,(C₁-C₆)-alkylhydroxyimino, (C₁-C₆)-alkoxyimino,(C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,(C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkyl sulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkyl-aminocarbonyl,di-(C₁-C₆)-alkyl-aminothiocarbonyl, (C₂-C₆)-alkenylaminocarbonyl,di-(C₂-C₆)-alkenylaminocarbonyl, (C₃-C₈)-cycloalkylaminocarbonyl,(C₁-C₆)-alkylsulfonylamino, (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino,aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,di-(C₁-C₆)-alkyl-aminosulfonyl, (C₁-C₆)-alkylsulfoximino,aminothiocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,di-(C₁-C₆)-alkyl-aminothiocarbonyl, (C₃-C₈)-cycloalkylamino,NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino), or where thesubstituents may independently be selected from phenyl or a 5- or6-membered heteroaromatic ring, where phenyl or the ring may optionallybe mono- or polysubstituted identically or differently by C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,NO₂, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, m is 0, 1 or 2, n is 0, 1 or
 2. 2.A compound of formula (I) according to claim 1 wherein Aa is —S(O)m-,—O—,—C(R⁸)(R⁹)— or carbonyl, Ab is —N(R⁷)—, —S(O)m-, —O— or—C(R¹⁰)(R¹¹)—, Ac is —N(R⁷)—, —C(R¹²)(R¹³)— or carbonyl, Ad is —N(R⁷)—,—O— or —C(R¹⁴)(R¹⁵)—, where not more than two of the Aa, Ab, Ac and Adsubstituents at the same time can be —N(R⁷)—, —O— or —S(O)m-, resultingin the structural units A1 to A12 below:

where the bond to the substituent Q is identified by a wavy line and thebond to the sulfur atom by an asterisk *, R¹ is (C₁-C₄)alkyl,(C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)alkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)alkynyloxy-(C₁-C₄)alkyl,(C₂-C₄)haloalkynyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylamino, di-(C₁-C₄)alkyl-amino,(C₃-C₆)cycloalkylamino, (C₁-C₄)alkylcarbonyl-amino,(C₁-C₄)alkylthio-(C₁-C₄)alkyl, (C₁-C₄)haloalkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylsulfinyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl,(C₁-C₄)haloalkylcarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonylamino, or isin each case optionally identically or differently mono- or di-aryl-,-hetaryl- or -heterocyclyl-substituted (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl, where aryl, hetarylor heterocyclyl are each optionally identically or differently mono- ordisubstituted by halogen, cyano, carbamoyl, aminosulfonyl, (C₁-C₄)alkyl,(C₃-C₄)cycloalkyl, (C₁-C₄)alkoxy, C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)alkylsulfimino, or R¹ is aryl, hetaryl or heterocyclyl, each ofwhich is optionally mono- or disubstituted identically or differently byhalogen, cyano, carbamoyl, (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-alkylsulfimino, (C₁-C₄)-alkylsulfoximino, (C₁-C₄)-alkylcarbonyl,(C₃-C₄)-trialkylsilyl, (═O) (in the case of heterocyclyl only) and (═O)₂(in the case of heterocyclyl only), R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵are independently hydrogen, cyano, halogen, nitro, acetyl, hydroxyl,amino, SCN, tri-(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,aminocarbonyl, (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,aminosulfonyl, (C₁-C₄)alkylaminosulfonyl, di-(C₁-C₄)alkylaminosulfonyl,aminothiocarbonyl, NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), andalso are phenyl or hetaryl, each of which is optionally mono- ordisubstituted identically or differently, where (in the case of hetaryl)at least one carbonyl group may optionally be present and/or wherepossible substituents are in each case as follows: cyano, halogen,nitro, acetyl, amino, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)haloalkyl-(C₁-C₄)alkoxyimino,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,aminocarbonyl, (C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,aminosulfonyl, (C₁-C₄)alkylaminosulfonyl, di-(C₁-C₄)alkylaminosulfonyl,NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), R⁷ is hydrogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)cyanoalkyl, (C₁-C₄)hydroxyalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl,(C₂-C₄)alkenyloxy-(C₁-C₄)alkyl, (C₂-C₄)haloalkenyloxy-(C₁-C₄)alkyl,(C₂-C₄)alkynyloxy-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkylthio-(C₁-C₄)alkyl,(C₁-C₄)alkylsulfinyl-(C₁-C₄)alkyl, (C₁-C₄)alkylsulfonyl-(C₁-C₄)alkyl or(C₁-C₄)alkylcarbonyl-(C₁-C₄)alkyl, Q is a heteroaromatic 8-, 9-, 10-,11- or 12-membered fused bicyclic or tricyclic ring system, where thering system is optionally mono- or polysubstituted identically ordifferently and where the substituents may independently be selectedfrom cyano, halogen, nitro, acetyl, hydroxyl, amino, SCN,tri-(C₁-C₆)-alkylsilyl, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₁-C₆)-cyanoalkyl, (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₆)-haloalkynyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl,(C₁-C₆)-cyanoalkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino, (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,(C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfinyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylaminocarbonyl,(C₁-C₆)-alkylsulfonylamino, (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino,aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,di-(C₁-C₆)-alkylaminosulfonyl, (C₁-C₆)-alkylsulfoximino,aminothiocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylamino,NHCO—(C₁-C₆)-alkyl ((C₁-C₆)-alkylcarbonylamino), or where thesubstituents may independently be selected from phenyl or a 5- or6-membered heteroaromatic ring, where phenyl or the ring may optionallybe mono- or polysubstituted identically or differently by C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, CN,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, n is 0, 1 or 2, m is 0, 1 or
 2. 3. Acompound of formula (I) according to claim 1 wherein Aa is —S(O)m-, —O—,—C(R⁸)(R⁹)— or carbonyl, Ab is —S(O)m-, —O— or —C(R¹⁰)(R¹¹)—, Ac is—C(R¹²)(R¹³)—, Ad is —O—, or —C(R¹⁴)(R¹⁵)—, where not more than two ofthe Aa, Ab and Ad substituents at the same time can be —O— or —S(O)m-,resulting in the following structural units: A1, A4, A6, A7, A8, A9,A12, R¹ is (C₁-C₄)-alkyl, (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-haloalkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-haloalkynyl, (C₃-C₆)-cycloalkyl,(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl or(C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴,R¹⁵ are independently hydrogen, cyano, halogen, nitro, hydroxyl, amino,SCN, tri-(C₁-C₄)alkylsilyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₄)alkenyl,(C₂-C₄)haloalkenyl, (C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl,(C₂-C₄)haloalkynyl, (C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)cyanoalkoxy, (C₁-C₄)alkylhydroxyimino,(C₁-C₄)alkoxyimino, (C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy,(C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, aminocarbonyl,(C₁-C₄)alkylaminocarbonyl, di-(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonylamino, (C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino,aminosulfonyl, (C₁-C₄)alkylaminosulfonyl, di-(C₁-C₄)alkyl-aminosulfonyl,NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), and also are phenyl orhetaryl, each of which is optionally mono- or disubstituted identicallyor differently, where (in the case of hetaryl) at least one carbonylgroup may optionally be present and/or where possible substituents arein each case as follows: cyano, halogen, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,halo(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)cyanoalkyl, (C₂-C₄)alkenyl, (C₂-C₄)haloalkenyl,(C₂-C₄)cyanoalkenyl, (C₂-C₄)alkynyl, (C₂-C₄)haloalkynyl,(C₂-C₄)cyanoalkynyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylhydroxyimino, (C₁-C₄)alkoxyimino,(C₁-C₄)alkyl-(C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylsulfonyloxy, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,(C₁-C₄)alkylamino, di-(C₁-C₄)alkylamino, aminosulfonyl,(C₁-C₄)alkylaminosulfonyl, di-(C₁-C₄)alkylaminosulfonyl,NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino), Q is a heteroaromatic9-membered or 12-membered fused bicyclic or tricyclic ring system fromthe group of Q1 to Q20,

R⁴ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,(C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl or(C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl, R⁵, R⁶ are independently hydrogen,cyano, halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,(C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyloxy,(C₁-C₄)-alkylcarbonyl, (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,(C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,(C₁-C₄)-alkylsulfonylamino, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,aminosulfonyl, (C₁-C₄)-alkylaminosulfonyl ordi-(C₁-C₄)-alkylaminosulfonyl, n is 0, 1 or 2, m is 0, 1 or
 2. 4. Acompound of formula (I) according to claim wherein Aa is —C(R⁸)(R⁹)— orcarbonyl, Ab is —C(R¹⁰)(R¹¹)—, Ac is —C(R¹²)(R¹³)—, Ad is —C(R¹⁴)(R¹⁵)—,resulting in the following structural units: A1, A12, R¹ is methyl,ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl,cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl, R⁸,R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ are independently hydrogen, cyano,halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, NHCO—(C₁-C₄)alkyl ((C₁-C₄)alkylcarbonylamino)or hydroxyl, Q is a heteroaromatic 9-membered or 12-membered fusedbicyclic or tricyclic ring system from the group of Q1, Q2, Q3, Q10,Q14, Q16, Q17, Q18, Q19 or Q20, R⁴ is (C₁-C₄)alkyl or(C₁-C₄)alkoxy-(C₁-C₄)-alkyl, R⁵ is hydrogen, cyano, halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₃-C₆)cycloalkyl, (C₁-C₄)alkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkoxyimino, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl, (C₁-C₄)alkylcarbonyl,(C₁-C₄)haloalkylcarbonyl, (C₁-C₄)alkylaminocarbonyl,di-(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonylamino,(C₁-C₄)alkylaminosulfonyl or di-(C₁-C₄)alkylaminosulfonyl, R⁶ ishydrogen, (C₁-C₄)alkyl or (C₁-C₄)haloalkyl, n is 0, 1 or
 2. 5. Acompound of formula (I) according to claim 1 wherein Aa is —C(R⁸)(R⁹)—or carbonyl, Ab is —C(R¹⁰)(R¹¹)—, Ac is —C(R¹²)(R¹³)—, Ad is—C(R¹⁴)(R¹⁵)—, resulting in the following structural units: A1, A12, R¹is methyl, ethyl, n-propyl, i-propyl, cyclopropyl, 2,2,2-trifluoroethylor 1,1-difluoroethyl, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ areindependently hydrogen, cyano, fluorine, chlorine, bromine, methyl,ethyl, trifluoromethyl, difluoromethyl or trifluoroethyl, Q is aheteroaromatic 9-membered fused bicyclic ring system from the group ofQ1, Q2, Q3, Q17 or Q18, R⁴ is methyl, ethyl, isopropyl, methoxymethyl ormethoxyethyl, R⁵ is fluorine, chlorine, bromine, fluoromethyl,difluoromethyl, trifluoromethyl, fluoroethyl (CH₂CFH₂, CHFCH₃),difluoroethyl (CF₂CH₃, CH₂CHF₂, CHFCFH₂), trifluoroethyl (CH₂CF₃,CHFCHF₂, CF₂CFH₂), tetrafluoroethyl (CHFCF₃, CF₂CHF₂), pentafluoroethyl,trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl,R⁶ is hydrogen, methyl, ethyl, n-propyl, i-propyl or difluoromethyl, nis 0, 1 or
 2. 6. A compound of formula (I) according to claim 1 whereinAa is —C(R⁸)(R⁹)— or carbonyl, Ab is —C(R¹⁰)(R¹¹)—, Ac is —C(R¹²)(R¹³)—,Ad is —C(R¹⁴)(R¹⁵)—, resulting in the following structural units: A1,A12 R¹ is methyl, ethyl or 2,2,2-trifluoroethyl, R⁸ is hydrogen, methyl,fluorine, chlorine or trifluoromethyl, R⁹ is hydrogen or hydroxyl, R¹⁰is hydrogen, methyl or trifluoromethyl, R¹¹ is hydrogen or methyl, R¹²is hydrogen, methyl or trifluoromethyl, R¹³ is hydrogen, R¹⁴ and R¹⁵ arehydrogen Q is a heteroaromatic 9-membered fused bicyclic ring systemfrom the group of Q1, Q2, Q3, Q17 or Q18, R⁴ is methyl, R⁵ istrifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl,trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl ortrifluoromethylsulfonyl, R⁶ is hydrogen, methyl, ethyl, i-propyl ordifluoromethyl, n is 0, 1 or
 2. 7. Agrochemical formulation comprising acompound of formula (I) according to claim 1 and one or more extendersand/or surfactants.
 8. Agrochemical formulation according to claim 7,additionally comprising further agrochemically active ingredient. 9.Method for controlling one or more animal pests, comprising allowing acompound of formula (I) according to claim 1 or an agrochemicalformulation thereof to act on the animal pests and/or a habitat thereof.10. A product comprising a compound of formula (I) according to claim 1or of agrochemical formulations thereof for controlling one or moreanimal pests.